Trifluoroacetic acid → HCID 46188945, compound

HRID 883129Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:9]([C:10]([N:12]([O:14]C(C)(C)C)[CH3:13])=[O:11])[N:8]=[C:7]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[F:26])[S:6]1.C(O)(C(F)(F)F)=O>>[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:9]([C:10]([N:12]([OH:14])[CH3:13])=[O:11])[N:8]=[C:7]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[F:26])[S:6]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86604847HCID 86604847, compound

Product 1

HCID 46188945HCID 46188945, compoundYield 49.2%

Procedure

To 2-(3-aminopropyl)-N-tert-butoxy-5-(2,5-difluorophenyl)-N-methyl-2-phenyl-1,3,4-thiadiazole-3(2H)-carboxamide (0.023 g, 0.05 mmol) was added TFA (2 mL). After stirring for 18 hours, the mixture was concentrated and chromatographed (10:1:0.2 dichloromethane/methanol/30% NH4OH) to provide the product (0.01 g, 49%). MS ESI (+) m/z 407 (M+1) detected; 1H NMR (400 MHz, CDCl3) δ 7.45 (d, 2H), 7.36 (m, 3H), 7.29 (m, 1H), 7.11 (m, 2H), 3.28 (s, 3H), 3.12 (m, 1H), 2.90 (m, 1H), 2.78 (m, 1H), 2.24 (m, 1H), 1.98 (m, 1H), 1.62 (m, 1H).

Workup

concentrationthe mixture was concentrated
customchromatographed (10:1:0.2 dichloromethane/methanol/30% NH4OH)

Sources & evidence

ORD record: ord-b0d7b321b738448a8f8e5f87a9460255
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236825B2

Reaction notes

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