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

HRID 570432Notes

Reaction equation

HRID 570432 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:43])([F:42])[O:33]C1C=C(C=CC=1)C=O>>[F:31][C:32]([F:43])([F:42])[O:33][C:30]1[CH:29]=[C:6]([CH:5]=[CH:4][CH:3]=1)[CH2:7][NH:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[S:15][CH:16]=[CH:17][C:18]=1[NH:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]2[NH:26][CH:27]=[CH:28][C:21]=12)=[O:13]

Participants

3

Reactant 2

HCID 6051393-(Trifluoromethoxy)benzaldehydeHCID 509244513-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid [2-(4-methoxy-benzylamino)-ethyl]-amide

Product 1

HCID 707956383-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid [2-(3-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 3-(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.) 10.29 (1H, s) 8.04 (1H, t, J=5.56 Hz) 8.01 (1H, d, J=5.42 Hz) 7.77 (1H, dd, J=5.42, 0.15 Hz) 7.47 (1H, d, J=5.37 Hz) 7.39 (1H, d, J=7.76 Hz) 7.26-7.35 (3H, m) 7.18 (1H, d, J=7.96 Hz) 6.80 (1H, d, J=5.42 Hz) 6.42 (1H, dd, J=3.47, 1.90 Hz) 3.74 (2H, s) 3.35 (2H, q, J=6.35 Hz) 2.63 (2H, t, J=6.49 Hz)

Sources & evidence

ORD record
ord-0f5feb05eb254ef59ece46bbcebddbac
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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