p-(Trifluoromethoxy)benzaldehyde → 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid [2-(4-trifluoromethoxy-benzylamino)-ethyl]-amide

HRID 570433Notes

Reaction equation

HRID 570433 reaction equation
COC1C=CC(C[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])=CC=1.[F:31][C:32]([F:43])([F:42])[O:33][C:34]1[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=1>>[F:31][C:32]([F:43])([F:42])[O:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][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:36][CH:35]=1

Participants

3

Reactant 2

HCID 69573p-(Trifluoromethoxy)benzaldehydeHCID 509244513-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid [2-(4-methoxy-benzylamino)-ethyl]-amide

Product 1

HCID 707956393-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid [2-(4-trifluoromethoxy-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-(trifluoromethoxy)benzaldehyde instead of 4-methoxy benzaldehyde. LCMS (ESI) 476 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.52 (1H, br. s.) 10.25 (1H, s) 8.04 (1H, t, J=5.52 Hz) 8.01 (1H, d, J=5.42 Hz) 7.77 (1H, d, J=5.47 Hz) 7.46 (1H, d, J=5.42 Hz) 7.42 (2H, d, J=8.69 Hz) 7.29 (1H, d, J=2.54 Hz) 7.23 (2H, d, J=8.44 Hz) 6.79 (1H, d, J=5.42 Hz) 6.43 (1H, dd, J=3.47, 1.90 Hz) 3.70 (2H, s) 3.35 (2H, q, J=6.49 Hz) 2.63 (2H, t, J=6.52 Hz)

Sources & evidence

ORD record
ord-d3205065481943a8ae7cecb287c062c5
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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