Reaction #619181

ord-f79b7faa9be94abe8fc30ce7ca847e0b

Reaction equation

CC1CCC(N(C(=O)Nc2ncc(C=O)s2)C2CCN(C(=O)OC(C)(C)C)CC2)CC1
4-[3-(5-formyl-thiazol-2-yl)-1-(4-methyl-cyclohexyl)-ureido]-piperidine-1-carboxylic acid tert-butyl ester
COC(=O)CC(=O)N1CCNCC1.Cl
3-oxo-3-piperazin-1-yl-propionic acid methyl ester hydrochloride
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
sodium triacetoxy-borohydride
→
COC(=O)CC(=O)N1CCN(Cc2cnc(NC(=O)N(C3CCC(C)CC3)C3CCN(C(=O)OC(C)(C)C)CC3)s2)CC1
desired product
Yield 25.0%
COC(=O)CC(=O)N1CCN(Cc2cnc(NC(=O)N(C3CCC(C)CC3)C3CCN(C(=O)OC(C)(C)C)CC3)s2)CC1
4-[3-{5-[4-(2-Methoxycarbonyl-acetyl)-piperazin-1-ylmethyl]-thiazol-2-yl}-1-(4-methyl-cyclohexyl)-ureido]-piperidine-1-carboxylic acid tert-butyl ester
Yield 25.0%

Reactants

CC1CCC(N(C(=O)Nc2ncc(C=O)s2)C2CCN(C(=O)OC(C)(C)C)CC2)CC1
4-[3-(5-formyl-thiazol-2-yl)-1-(4-methyl-cyclohexyl)-ureido]-piperidine-1-carboxylic acid tert-butyl ester
COC(=O)CC(=O)N1CCNCC1.Cl
3-oxo-3-piperazin-1-yl-propionic acid methyl ester hydrochloride
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
sodium triacetoxy-borohydride

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherPrepared

Procedure

Prepared as described in general procedure (P) using 4-[3-(5-formyl-thiazol-2-yl)-1-(4-methyl-cyclohexyl)-ureido]-piperidine-1-carboxylic acid tert-butyl ester (68 mg, 0.15 mmol), 3-oxo-3-piperazin-1-yl-propionic acid methyl ester hydrochloride (54 mg, 0.19 mmol) and sodium triacetoxy-borohydride (38 mg, 0.18 mmol) to afford 23 mg (25%) of the desired product after purification.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: USRE045183E1uspto-grants-2014_10