Trifluoroacetic acid → Trifluoroacetic acid

HRID 605154Notes

Reaction equation

HRID 605154 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9](=[O:48])[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24](=[O:33])[NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([Br:32])[CH:27]=3)=[CH:20][C:19]=2[NH:34][C:35]2[C:36]3[CH:44]=[CH:43][C:42]([CH:45]([CH3:47])[CH3:46])=[N:41][C:37]=3[N:38]=[CH:39][N:40]=2)[CH:12]=1)(C)(C)C.[F:50][C:51]([F:56])([F:55])[C:52]([OH:54])=[O:53]>>[NH2:7][CH2:8][C:9]([NH:10][C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=1)[O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([Br:32])[CH:27]=2)=[O:33])=[CH:20][C:19]=1[NH:34][C:35]1[C:36]2[CH:44]=[CH:43][C:42]([CH:45]([CH3:47])[CH3:46])=[N:41][C:37]=2[N:38]=[CH:39][N:40]=1)=[O:48].[F:50][C:51]([F:56])([F:55])[C:52]([OH:54])=[O:53]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67040880HCID 67040880, compound

Product 2

HCID 6422Trifluoroacetic acidYield 98%HCID 67040802HCID 67040802, compound

Procedure

The product of Example 110 (0.04 g, 0.055 mmol) was treated with trifluoroacetic acid as in the procedure for Example 96. The crude product was purified by trituration in dichloromethane to provide the title compound as a trifluoroacetic acid salt (0.046 g, 98%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.33 (d, J=6.99 Hz, 6 H), 3.21-3.32 (m, 1 H), 3.75 (d, J=5.52 Hz, 2 H), 6.81 (d, J=9.19 Hz, 1 H), 7.14 (d, J=8.82 Hz, 1 H), 7.24-7.38 (m, 3 H), 7.45 (s, 1 H), 7.72-7.78 (m, 1 H), 7.81 (d, J=8.46 Hz, 1 H), 8.02 (dd, J=8.82, 2.21 Hz, 1 H), 8.10 (s, 3 H), 8.18 (d, J=1.84 Hz, 1 H), 8.80 (s, 1 H), 8.92 (d, J=8.46 Hz, 1 H), 10.45 (s, 1 H), 11.26 (s, 1 H).

Workup

  1. customThe crude product was purified by trituration in dichloromethane

Sources & evidence

ORD record
ord-284c097df37947c9a5ceefa24faed9f3
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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