Trifluoroacetic acid → HCID 86670629, compound

HRID 2370058Notes

Reaction equation

C(OC([NH:8][CH:9]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:10]([O:12][C:13]1[CH:14]=[N:15][C:16](/[CH:19]=[C:20]2\[NH:21][C:22](=[O:34])/[C:23](=[CH:27]/[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)/[NH:24][C:25]\2=[O:26])=[CH:17][CH:18]=1)=[O:11])=O)(C)(C)C.[F:41][C:42]([F:47])([F:46])[C:43]([OH:45])=[O:44]>ClCCl>[F:41][C:42]([F:47])([F:46])[C:43]([O-:45])=[O:44].[CH:27](=[C:23]1/[NH:24][C:25](=[O:26])/[C:20](=[CH:19]/[C:16]2[N:15]=[CH:14][C:13]([O:12][C:10](=[O:11])[CH:9]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[NH3+:8])=[CH:18][CH:17]=2)/[NH:21][C:22]/1=[O:34])/[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Compound 8 (0.126 g) was dissolved in 10 mL of dichloromethane and then 2.5 mL of trifluoroacetic acid was added slowly at 0° C. The reaction mixture was stirred at 0° C. and monitored by TLC until the starting material disappeared. It was concentrated by rotary evaporator to a give a crude compound, which was recrystallized in acetonitrile to give Compound 9 as a yellow solid (71%). mp 280° C.; 1H-NMR (400 MHz, DMSO): δ 5.69 (s, 1H), 6.79 (s, 1H), 6.86 (s, 1H), 7.34-7.38 (m, 1H), 7.44 (dd, J=7.6 Hz, 7.6 Hz, 2H), 7.55-7.58 (m, 5H), 7.65-7.67 (m, 2H), 7.71-7.74 (m, 1H), 7.80-7.82 (m, 1H), 8.59 (s, 1H), 8.91 (br, 3H), 10.42 (br, 1H), 12.16 (s, 1H).

Workup

concentrationIt was concentrated by rotary evaporator to
customa give a crude compound, which
customwas recrystallized in acetonitrile

Sources & evidence

ORD record: ord-07e32b0a58a845aca7cbdd6127c943c3
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710062B2

Reaction notes

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