Methanol → HCID 86729619, compound

HRID 2284892Notes

Reaction equation

HRID 2284892 reaction equation
[C:1]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][N:16]=[C:15]([NH:23][C@H:24]2[CH2:29][CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25]2)[N:14]=1)(=[O:4])[CH:2]=[CH2:3].FC(F)(F)C(O)=O.CO>C(Cl)Cl>[NH:26]1[CH2:27][CH2:28][CH2:29][C@H:24]([NH:23][C:15]2[N:14]=[C:13]([NH:12][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[NH:5][C:1](=[O:4])[CH:2]=[CH2:3])[C:18]([C:19]([F:22])([F:20])[F:21])=[CH:17][N:16]=2)[CH2:25]1

Participants

5

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 86729620HCID 86729620, compound

Product 1

HCID 86729619HCID 86729619, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)-tert-butyl 3-(4-(2-acrylamidophenylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)piperidine-1-carboxylate (3 g) in DCM (30 ml) was added trifluoroacetic acid (5 ml) at 0° C. for 10 min and stirred at rt for 2 h. TLC showed completion of starting material. (TLC system: 15% methanol in dichloromethane, Rf=0.2). The reaction mixture was concentrated, and the crude was co-distilled with DCM (3×20 mL) and washed with diethyl ether (2×10 mL) to obtain (S)—N-(2-(2-(piperidin-3-ylamino)-5-(trifluoromethyl) pyrimidin-4-ylamino)phenyl)acrylamide as an off white solid. (3 g, 97%). MS: m/z=407.1 (ES+, M+H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washwashed with diethyl ether (2×10 mL)

Sources & evidence

ORD record
ord-e1dcf8d6ee004f888d228793055b8d1e
Source dataset
uspto-grants-2015_09
Patent number
US09145387B2

Reaction notes

Loading…