Benzaldehyde → (4-Benzylamino-piperidin-1-yl)-[3-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)-thiophen-2-yl]-methanone

HRID 570446Notes

Reaction equation

HRID 570446 reaction equation
CO[C:3]1[CH:30]=[CH:29][C:6]([CH2:7]NCCNC(C2SC=CC=2NC2C=CN=C3NC=CC=23)=O)=[CH:5][CH:4]=1.[NH2:31][CH:32]1[CH2:37][CH2:36][N:35]([C:38]([C:40]2[S:41][CH:42]=[CH:43][C:44]=2[NH:45][C:46]2[CH:51]=[CH:50][N:49]=[C:48]3[NH:52][CH:53]=[CH:54][C:47]=23)=[O:39])[CH2:34][CH2:33]1.C(=O)C1C=CC=CC=1>>[CH2:7]([NH:31][CH:32]1[CH2:37][CH2:36][N:35]([C:38]([C:40]2[S:41][CH:42]=[CH:43][C:44]=2[NH:45][C:46]2[CH:51]=[CH:50][N:49]=[C:48]3[NH:52][CH:53]=[CH:54][C:47]=23)=[O:39])[CH2:34][CH2:33]1)[C:6]1[CH:29]=[CH:30][CH:3]=[CH:4][CH:5]=1

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 509244513-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid [2-(4-methoxy-benzylamino)-ethyl]-amideHCID 66958092(4-Amino-piperidin-1-yl)-[3-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)-thiophen-2-yl]-methanone

Product 1

HCID 66957993(4-Benzylamino-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-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid [2-(4-methoxy-benzylamino)-ethyl]-amide using (4-Amino-piperidin-1-yl)-[3-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)-thiophen-2-yl]-methanone instead of 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid (2-amino-ethyl)-amide and benzaldehyde instead of 4-methoxy benzaldehyde. LCMS (ESI) 432 1H NMR (400 MHz, DMSO-d6) δ ppm 11.33 (1H, s) 8.93 (1H, s) 7.86 (1H, d, J=5.27 Hz) 7.70 (1H, d, J=5.27 Hz) 7.20-7.27 (3H, m) 7.11-7.19 (2H, m) 6.53 (1H, dd, J=3.51, 1.95 Hz) 6.43 (1H, d, J=5.47 Hz) 3.90 (2H, d, J=13.08 Hz) 3.57 (2H, s) 2.91 (2H, t, J=10.84 Hz) 1.63 (2H, d, J=10.35 Hz) 1.04-1.15 (2H, m)

Sources & evidence

ORD record
ord-c4219063021e4777acb2ab718d88d617
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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