Trifluoroacetic acid → HCID 86615541, compound

HRID 605058Notes

Reaction equation

C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:29])[NH:22][C:23]3[S:24][C:25]([Br:28])=[CH:26][N:27]=3)=[CH:17][C:16]=2[NH:30][C:31]2[C:32]3[CH:40]=[CH:39][C:38]([CH:41]([CH3:43])[CH3:42])=[N:37][C:33]=3[N:34]=[CH:35][N:36]=2)=[CH:10][CH:9]=1)(C)(C)C.FC(F)(F)C(O)=O>>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([NH:22][C:23]3[S:24][C:25]([Br:28])=[CH:26][N:27]=3)=[O:29])=[CH:17][C:16]=2[NH:30][C:31]2[C:32]3[CH:40]=[CH:39][C:38]([CH:41]([CH3:43])[CH3:42])=[N:37][C:33]=3[N:34]=[CH:35][N:36]=2)=[CH:10][CH:9]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86615542HCID 86615542, compound

Product 1

HCID 86615541HCID 86615541, compoundYield 76%

Procedure

The product of Example 15B was reacted with trifluoroacetic acid using the procedure form Example 13E to provide the crude title compound which was purified by column chromatography on silica gel using methanol/dichloromethane as eluent to provide the title compound (120 mg, 76%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.34 (d, J=6.99 Hz, 6 H) 3.15-3.30 (m, 1 H) 5.64 (s, 2 H) 6.65 (d, J=8.46 Hz, 2 H) 6.84 (d, J=8.46 Hz, 1 H) 7.15 (d, J=8.46 Hz, 2 H) 7.65 (d, J=8.46 Hz, 1 H) 7.64 (s, 1 H) 7.92 (dd, J=8.46, 1.84 Hz, 1 H) 8.10 (d, J=1.47 Hz, 1 H) 8.59 (s, 1 H) 8.89 (d, J=8.46 Hz, 1 H) 10.14 (s, 1 H) 12.85 (s, 1 H); MS (ESI+) m/z 592/594 (M+H)+.

Workup

customto provide the crude title compound which
customwas purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-f163c415734f4bd798fccc9316a77220
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910595B2

Reaction notes

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