Tert-butyl 1-aminopiperidine-4-carboxylate → (4-Amino-piperidin-1-yl)-[3-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)-thiophen-2-yl]-methanone

HRID 570445Notes

Reaction equation

HRID 570445 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][C:14]([C:16]2[S:17][CH:18]=[CH:19][C:20]=2[NH:21][C:22]2[CH:27]=[CH:26][N:25]=[C:24]3[NH:28][CH:29]=[CH:30][C:23]=23)=[O:15])C1)=O)(C)(C)C.[C:31]([CH:38]1CCN(N)CC1)(OC(C)(C)C)=O>>[NH2:8][CH:12]1[CH2:38][CH2:31][N:13]([C:14]([C:16]2[S:17][CH:18]=[CH:19][C:20]=2[NH:21][C:22]2[CH:27]=[CH:26][N:25]=[C:24]3[NH:28][CH:29]=[CH:30][C:23]=23)=[O:15])[CH2:10][CH2:11]1

Participants

3

Reactant 2

HCID 21899493Tert-butyl 1-aminopiperidine-4-carboxylateHCID 669579823-{[3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 66958092(4-Amino-piperidin-1-yl)-[3-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)-thiophen-2-yl]-methanone

Procedure

This compound was prepared in an analogous manner as 3-{[3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester using 4-Boc-aminopiperidine instead of 1-BOC-3-aminopyrrolidine. LCMS (ESI) 342 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 12.52 (1H, s) 10.36 (1H, s) 8.18 (1H, d, J=4.10 Hz) 8.04 (1H, d, J=7.03 Hz) 7.87 (1H, d, J=5.08 Hz) 7.33-7.37 (1H, m) 7.15 (1H, d, J=5.27 Hz) 6.53 (1H, d, J=7.03 Hz) 3.54 (4H, s) 2.81-2.94 (1H, m) 1.82 (2H, d, J=9.96 Hz) 1.70-1.76 (1H, m) 1.25-1.39 (2H, m)

Sources & evidence

ORD record
ord-2c1d488381b1429da669e1bcc9fe7a0a
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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