4-Methoxybenzaldehyde → 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid [2-(4-trifluoromethyl-benzylamino)-ethyl]-amide

HRID 570434Notes

Reaction equation

HRID 570434 reaction equation
CO[C:3]1[CH:30]=[CH:29][C:6]([CH2:7][NH:8][CH2:9][CH2:10][NH:11][C:12]([C:14]2[S:15][CH:16]=[CH:17][C:18]=2[NH:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22]3[NH:26][CH:27]=[CH:28][C:21]=23)=[O:13])=[CH:5][CH:4]=1.[F:31][C:32]([F:42])([F:41])C1C=CC(C=O)=CC=1.COC1C=CC(C=O)=CC=1>>[F:31][C:32]([F:42])([F:41])[C:3]1[CH:30]=[CH:29][C:6]([CH2:7][NH:8][CH2:9][CH2:10][NH:11][C:12]([C:14]2[S:15][CH:16]=[CH:17][C:18]=2[NH:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22]3[NH:26][CH:27]=[CH:28][C:21]=23)=[O:13])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 312444-MethoxybenzaldehydeHCID 679964-(Trifluoromethyl)benzaldehydeHCID 509244513-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid [2-(4-methoxy-benzylamino)-ethyl]-amide

Product 1

HCID 707955153-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid [2-(4-trifluoromethyl-benzylamino)-ethyl]-amide

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-(trifluoromethyl)benzaldehyde lidine instead of 4-methoxy benzaldehyde. LCMS (ESI) 460 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.52 (1H, br. s.) 10.25 (1H, s) 8.05 (1H, t, J=5.66 Hz) 8.01 (1H, d, J=5.47 Hz) 7.77 (1H, d, J=5.27 Hz) 7.58-7.64 (2H, m) 7.50-7.55 (2H, m) 7.46 (1H, d, J=5.42 Hz) 7.30 (1H, d, J=3.17 Hz) 6.79 (1H, d, J=5.52 Hz) 6.43 (1H, dd, J=3.44, 1.93 Hz) 3.77 (2H, s) 3.35 (2H, q, J=6.23 Hz) 2.63 (2H, t, J=6.52 Hz)

Sources & evidence

ORD record
ord-3211017d0a1e4e2985636f9e80ca4ebf
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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