Trifluoroacetic acid → HCID 46188945, compound

HRID 270531Notes

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-d2943b44f4984ff4a67989d9a222b34c
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07449486B2

Reaction notes

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