2-Methylphenethylamine → 3-(7H-Pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid (2-o-tolyl-ethyl)-amide

HRID 570505Notes

Reaction equation

HRID 570505 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:12][CH:13]=[CH:14][C:15]=1[NH:16][C:17]1[C:18]2[CH:25]=[CH:24][NH:23][C:19]=2[N:20]=[CH:21][N:22]=1)=[O:10])C1C=CC=CC=1.[CH3:26][C:27]1[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=1[CH2:29]CN>>[C:27]1([CH3:26])[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=1[CH2:29][CH2:1][NH:8][C:9]([C:11]1[S:12][CH:13]=[CH:14][C:15]=1[NH:16][C:17]1[C:18]2[CH:25]=[CH:24][NH:23][C:19]=2[N:20]=[CH:21][N:22]=1)=[O:10]

Participants

3

Reactant 2

HCID 20638682-MethylphenethylamineHCID 509238613-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid benzylamide

Product 1

HCID 509239923-(7H-Pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid (2-o-tolyl-ethyl)-amideYield 39%

Procedure

The title compound was prepared in an analogous manner as 3-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid benzylamide using 2-methylphenethylamine instead of benzylamine and obtained in 39% yield (HPLC: 95%, RT: 6.67 min). 1H NMR (DMSO-d6) 11.98 (br s, 1H), 11.43 (s, 1H), 8.48 (d, J=5.5 Hz, 1H), 8.42-8.36 (m, 2H), 7.76 (d, J=5.5 Hz, 1H), 7.37 (dd, J=3.3, 2.2 Hz, 1H), 7.18-7.10 (m, 4H), 6.46 (dd, J=3.7, 1.8 Hz, 1H), 3.47-3.43 (m, 2H), 2.86 (t, J=7.9 Hz, 2H), 2.36 (s, 3H); MS (m/z) 378 [M+H]+.

Workup

  1. customobtained in 39% yield (HPLC: 95%, RT: 6.67 min)

Sources & evidence

ORD record
ord-dcb04a704f724eee9c69ef773ea2be1c
Source dataset
uspto-grants-2015_05
Patent number
US09023847B2

Reaction notes

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