Trifluoroacetic acid → Trifluoroacetic acid

HRID 1662824Notes

Reaction equation

HRID 1662824 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]3[N:29]=[CH:28][C:27]([NH:30][C:31](=[O:47])[C:32]4[CH:37]=[C:36]([NH:38][C:39]([C:41]5[S:42][CH:43]=[CH:44][CH:45]=5)=[O:40])[CH:35]=[CH:34][C:33]=4[Cl:46])=[CH:26][N:25]=3)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.[C:48]([OH:54])([C:50]([F:53])([F:52])[F:51])=[O:49]>C(Cl)Cl>[Cl:46][C:33]1[CH:34]=[CH:35][C:36]([NH:38][C:39]([C:41]2[S:42][CH:43]=[CH:44][CH:45]=2)=[O:40])=[CH:37][C:32]=1[C:31](=[O:47])[NH:30][C:27]1[CH:28]=[N:29][C:24]([NH:23][C:20]2[CH:19]=[CH:18][C:17]([S:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)(=[O:15])=[O:16])=[CH:22][CH:21]=2)=[N:25][CH:26]=1.[C:48]([OH:54])([C:50]([F:53])([F:52])[F:51])=[O:49]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 596527044-[4-(5-{2-Chloro-5-[(Thiophene-2-Carbonyl)-Amino]-Benzoylamino}-Pyrimidin-2-ylamino)-Benzenesulfonyl]-Piperidine-1-Carboxylic Acid tert-Butyl Ester

Product 2

HCID 6422Trifluoroacetic acidYield 87%HCID 24960368Thiophene-2-Carboxylic Acid (4-Chloro-3-{2-[4-(Piperidine-4-Sulfonyl)-Phenylamino]-Pyrimidin-5-ylcarbamoyl}-Phenyl)-Amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred suspension of intermediate 26 (Example 37) (0.10 g, 0.143 mmol) in DCM (8 mL) was treated with TFA (0.200 mL) and stirred for 3 h. Solvents were then removed yielding desired product as TFA salt (0.075 g, 87%). 1H NMR (DMSO-d6): δ 1.61-1.70 (m, 2H), 2.01-2.04 (m, 2H), 2.80-2.90 (m, 2H), 7.23-7.27 (m, 1H), 7.58 (d, J=8.8 Hz, 1H), 7.74 (d, J=8.9 Hz, 2H), 7.86-7.91 (m, 2H), 8.04-8.05 (m, 4H), 8.21-8.25 (m, 1H), 8.65-8.69 (m, 1H), 8.9 (s, 2H), 10.37 (s, 1H), 10.53 (s, 1H), 10.79 (s, 1H).

Workup

  1. customSolvents were then removed

Sources & evidence

ORD record
ord-4dcd1a6e418a441cab47538cbecd86d3
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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