Réaction #43597

ord-f72d5f9f6cf8417da55a79919becba0b

Équation de réaction

CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F
HATU
N[C@H]1CCN(CC2Cn3c(=O)ccc4ncc(Cl)c2c43)C[C@H]1O
racemic 4-{[(3R,4S)-4-amino-3-hydroxy-1-piperidinyl]methyl}-3-chloro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one
O=C1CSc2ccc(C(=O)O)nc2N1
3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid
CCN(CC)CC
triethylamine
→
O=C1CSc2ccc(C(=O)N[C@H]3CCN(CC4Cn5c(=O)ccc6ncc(Cl)c4c65)C[C@H]3O)nc2N1
title compound
Rendement 59.0%
O=C1CSc2ccc(C(=O)N[C@H]3CCN(CC4Cn5c(=O)ccc6ncc(Cl)c4c65)C[C@H]3O)nc2N1
N-{(3R,4S)-1-[(3-Chloro-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl)methyl]-3-hydroxy-4-piperidinyl}-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxamide
Rendement 59.0%

Réactifs

CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F
HATU
N[C@H]1CCN(CC2Cn3c(=O)ccc4ncc(Cl)c2c43)C[C@H]1O
racemic 4-{[(3R,4S)-4-amino-3-hydroxy-1-piperidinyl]methyl}-3-chloro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one
O=C1CSc2ccc(C(=O)O)nc2N1
3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid
CCN(CC)CC
triethylamine

Réactifs

Aucun

Solvants

CN(C)C=O
DMF

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

The free base of the title compound was synthesised from racemic 4-{[(3R,4S)-4-amino-3-hydroxy-1-piperidinyl]methyl}-3-chloro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one (79 mg), 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid (for a synthesis see WO2003087098, Example 301(b)) (50 mg), triethylamine (0.066 ml) and HATU (95 mg) in DMF (2 ml) according to the general method of Example 9 in 59% yield.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07732461B2uspto-grants-2010_06