Trifluoroacetic acid → HCID 50923995, compound

HRID 570510Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C:15]([C:17]2[S:18][CH:19]=[CH:20][C:21]=2[NH:22][C:23]2[C:24]3[CH:31]=[CH:30][NH:29][C:25]=3[N:26]=[CH:27][N:28]=2)=[O:16])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C:15]([C:17]2[S:18][CH:19]=[CH:20][C:21]=2[NH:22][C:23]2[C:24]3[CH:31]=[CH:30][NH:29][C:25]=3[N:26]=[CH:27][N:28]=2)=[O:16])[CH2:9]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a 20 mL flask with magnetic stir bar was added 3-{[3-(7H-Pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester (100 mg, 0.23 mmol) in dichloromethane (2 mL). To the stirred solution was added trifluoroacetic acid (2.0 mL, 26.0 mmol) and the solution was stirred at 25° C. for 1 h. The solution was concentrated on a rotary evaporator and purified by preparative HPLC to afford 3-(7H-Pyrrolo[2,3-d]pyrimidin-4-ylamino)-thiophene-2-carboxylic acid piperidin-3-ylamide as a yellow solid (14 mg, 13%) (HPLC: 99%, RT: 2.81 min). 1H NMR (DMSO-d6) 12.02 (br s, 1H), 11.30 (s, 1H), 8.68-8.52 (m, 1H), 8.47 (d, J=5.5 Hz, 1H), 8.40 (s, 1H), 8.23 (d, J=7.7 Hz, 1H), 7.82 (d, J=5.5 Hz, 1H), 7.38 (dd, J=3.3, 2.2 Hz, 1H), 6.43 (dd, J=3.6, 1.8 Hz, 1H), 4.31-4.18 (m, 1H), 3.40-3.17 (m, 2H), 2.89-2.77 (m, 2H), 1.96-1.85 (m, 2H), 1.74-1.60 (m, 2H); MS (m/z) 343 [M+H]+.

Workup

concentrationThe solution was concentrated on a rotary evaporator
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-d8ec22b0f9254f988f468c70212da0a1
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023847B2

Reaction notes

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