Reaction #155371

ord-62aca8cd28694b80a8c88a8665d54cf6

Reaction equation

CC(C)(C)OC(=O)NCCCCN
(4-amino-butyl)-carbamic acid tert-butyl ester
Cn1c(CNc2ccc(C#N)cc2)nc2cc(C(=O)N(CCC(=O)O)c3ccccc3)ccc21
1e
Cn1c(CNc2ccc(C#N)cc2)nc2cc(C(=O)N(CCC(=O)O)c3ccccc3)ccc21
3-({2-[(4-Cyano-phenylamino)-methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}-phenyl-amino)-propionic acid
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F
2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate
CN1CCOCC1
N-methyl-morpholin
Cn1c(CNc2ccc(C#N)cc2)nc2cc(C(=O)N(CCC(=O)NCCCCNC(=O)OC(C)(C)C)c3ccccc3)ccc21
{4-[3-({2-[(4-Cyano-phenylamino)-methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}-phenyl-amino)-propionylamino]-butyl}-carbamic acid tert-butyl ester

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

A solution of the product of 1e (5.23 mmol), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU, 5.23 mmol) and N-methyl-morpholin (5.23 mmol) in 20 mL DMF was stirred at room temperature for 30 minutes. Then (4-amino-butyl)-carbamic acid tert-butyl ester (5.23 mmol) was added and the mixture stirred at room temperature for another 24 hours. The mixture was then diluted with water (100 mL) and the product was isolated through extraction with ethyl acetate.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08821871B2uspto-grants-2014_09