tert-butyl (2R)-2-(aminomethyl)pyrrolidine-1-carboxylate → (R)-2-({[3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carbonyl]-amino}methyl)pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 570468Notes

Reaction equation

HRID 570468 reaction equation
NCCN[C:5]([C:7]1[S:8][CH:9]=[CH:10][C:11]=1[NH:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]2[NH:19][CH:20]=[CH:21][C:14]=12)=[O:6].[NH2:22][CH2:23][C@H:24]1[CH2:28][CH2:27][CH2:26][N:25]1[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>>[C:32]([O:31][C:29]([N:25]1[CH2:26][CH2:27][CH2:28][C@@H:24]1[CH2:23][NH:22][C:5]([C:7]1[S:8][CH:9]=[CH:10][C:11]=1[NH:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]2[NH:19][CH:20]=[CH:21][C:14]=12)=[O:6])=[O:30])([CH3:35])([CH3:34])[CH3:33]

Participants

3

Reactant 2

HCID 1512534tert-butyl (2R)-2-(aminomethyl)pyrrolidine-1-carboxylateHCID 509244533-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid (2-amino-ethyl)-amide

Product 1

HCID 66957829(R)-2-({[3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carbonyl]-amino}methyl)pyrrolidine-1-carboxylic acid tert-butyl ester

Procedure

This compound was prepared in an analogous manner as 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid (2-amino-ethyl)-amide using (R)-2-(aminomethyl)-1-N-BOC-pyrrolidine instead of tert-butyl-2-amino ethyl carbamate. LCMS (ESI) 442 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.52 (1H, br. s.) 10.48 (1H, br. s.) 10.24 (1H, br. s.) 8.17 (1H, br. s.) 8.02 (1H, d, J=5.47 Hz) 7.79 (1H, d, J=5.27 Hz) 7.44-7.54 (1H, m) 7.31 (1H, d, J=2.73 Hz) 6.82 (1H, br. s.) 6.41 (1H, br. s.) 3.93 (1H, br. s.) 3.39 (1H, br. s.) 3.23 (2H, br.s.) 1.67-1.88 (4H, m) 1.39 (9H, s)

Sources & evidence

ORD record
ord-0301f956f0884fb08cef8212c1128684
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

Loading…