Trifluoroacetic acid → Trifluoroacetic acid

HRID 1662828Notes

Reaction equation

HRID 1662828 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:50])[C:32]4[CH:37]=[C:36]([NH:38][C:39](=[O:48])[C:40]5[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=5)[CH:35]=[CH:34][C:33]=4[Cl:49])=[CH:26][N:25]=3)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.[C:51]([OH:57])([C:53]([F:56])([F:55])[F:54])=[O:52]>C(Cl)Cl>[Cl:49][C:33]1[CH:34]=[CH:35][C:36]([NH:38][C:39](=[O:48])[C:40]2[CH:41]=[CH:42][C:43]([O:46][CH3:47])=[CH:44][CH:45]=2)=[CH:37][C:32]=1[C:31]([NH:30][C:27]1[CH:26]=[N:25][C:24]([NH:23][C:20]2[CH:19]=[CH:18][C:17]([S:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)(=[O:15])=[O:16])=[CH:22][CH:21]=2)=[N:29][CH:28]=1)=[O:50].[C:51]([OH:57])([C:53]([F:56])([F:55])[F:54])=[O:52]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 596527184-(4-{5-[2-Chloro-5-(4-Methoxy-Benzoylamino)-Benzoylamino]-Pyrimidin-2-ylamino}-Benzenesulfonyl)-Piperidine-1-Carboxylic Acid tert-Butyl Ester

Product 2

HCID 6422Trifluoroacetic acidYield 99%HCID 249607312-Chloro-5-(4-Methoxy-Benzoylamino)-N-{2-[4-(Piperidine-4-Sulfonyl)-Phenylamino]-Pyrimidin-5-yl}-Benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred suspension of intermediate 28 (Example 41) (0.075 g, 0.104 mmol) in DCM (8 mL) was treated with TFA (0.200 mL) and stirred for 18 h. Solvents were then removed yielding desired product as TFA salt (0.064 g, 99%). 1H NMR (DMSO-d6): δ 1.64-1.70 (m, 2H), 2.01-2.04 (m, 2H), 2.86-2.88 (m, 2H), 3.44-3.48 (m, 1H), 3.84 (s, 3H), 7.08 (d, J=8.8 Hz, 2H), 7.56 (d, J=8.9 Hz, 1H), 7.74 (d, J=8.8 Hz, 2H), 7.90 (dd, J=8.7 Hz, J=2.5 Hz, 1H), 7.98 (d, J=8.9 Hz, 2H), 8.05 (d, J=8.8 Hz, 2H), 8.23 (d, J=2.5 Hz, 1H), 8.24 (br s, 1H), 8.68 (br s, 1H), 8.90 (s, 2H), 10.37 (s, 1H), 10.39 (s, 1H), 10.78 (s, 1H).

Workup

  1. customSolvents were then removed

Sources & evidence

ORD record
ord-ee319e62a7604135a2810b691dc560f8
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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