Trifluoroacetic acid → Trifluoroacetic acid

HRID 1662812Notes

Reaction equation

HRID 1662812 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:52])[C:32]4[CH:37]=[C:36]([NH:38][C:39](=[O:50])[C:40]5[CH:45]=[CH:44][CH:43]=[C:42]([C:46]([F:49])([F:48])[F:47])[CH:41]=5)[CH:35]=[CH:34][C:33]=4[Cl:51])=[CH:26][N:25]=3)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.[C:53]([OH:59])([C:55]([F:58])([F:57])[F:56])=[O:54]>C(Cl)Cl>[Cl:51][C:33]1[CH:34]=[CH:35][C:36]([NH:38][C:39](=[O:50])[C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([C:46]([F:47])([F:48])[F:49])[CH:41]=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:21]=[CH:22][C:17]([S:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)(=[O:16])=[O:15])=[CH:18][CH:19]=2)=[N:29][CH:28]=1)=[O:52].[C:53]([OH:59])([C:55]([F:58])([F:57])[F:56])=[O:54]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 596527424-(4-{5-[2-Chloro-5-(3-Trifluoromethyl-Benzoylamino)-Benzoylamino]-Pyrimidin-2-ylamino}-Benzenesulfonyl)-Piperidine-1-Carboxylic Acid tert-Butyl Ester

Product 2

HCID 6422Trifluoroacetic acidYield 99%HCID 249603672-Chloro-N-{2-[4-(Piperidine-4-Sulfonyl)-Phenylamino]-Pyrimidin-5-yl}-5-(3-Trifluoromethyl-Benzoylamino)-Benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred suspension of intermediate 14 (Example 21) (0.058 g, 0.076 mmol) in DCM (8 mL) was treated with TFA (0.100 mL) and stirred for 3 h. Solvents were then removed yielding desired product as TFA salt (0.05 g, 99%). 1H NMR (DMSO-d6): δ 1.62-1.70 (m, 2H), 2.01-2.08 (m, 4H), 2.8-2.9 (m, 2H), 3.3-3.6 (m, 2H), 3.45-3.49 (m, 1H), 7.61 (d, J=8.8 Hz, 1H), 7.74 (d, J=8.8 Hz, 2H), 7.81 (t, J=15.7 Hz, J=7.8 Hz, 1H), 7.93 (dd, J=8.8 Hz, J=2.5 Hz, 1H), 8.00 (d, J=7.6 Hz, 1H), 8.05 (d, J=8.9 Hz, 2H), 8.10 (d, J=2.5 Hz, 1H), 8.20-8.32 (m, 3H), 8.65-8.69 (m, 1H), 8.90 (s, 2H), 10.37 (s, 1H), 10.76 (s, 1H), 10.80 (s, 1H).

Workup

  1. customSolvents were then removed

Sources & evidence

ORD record
ord-196fa5aafef444e995ee458a1f4d640d
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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