Trifluoroacetic acid methylene chloride → N-((S)-2-Amino-3-(4-(trifluoromethyl)phenyl)propyl)-5-(3-fluoroisoquinolin-6-yl)-1,3,4-thiadiazol-2-amine trifluoroacetate

HRID 2075394Notes

Reaction equation

[F:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12]1[S:16][C:15]([NH:17][CH2:18][C@@H:19]([NH:31]C(=O)OC(C)(C)C)[CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)=[N:14][N:13]=1)=[CH:7][CH:6]=2.[C:39]([OH:45])([C:41]([F:44])([F:43])[F:42])=[O:40].C(Cl)Cl>>[F:42][C:41]([F:44])([F:43])[C:39]([OH:45])=[O:40].[NH2:31][C@@H:19]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:28])([F:30])[F:29])=[CH:23][CH:22]=1)[CH2:18][NH:17][C:15]1[S:16][C:12]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[CH:4]=[N:3][C:2]([F:1])=[CH:11]3)=[N:13][N:14]=1

Participants

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chloride

HCID 57991856tert-Butyl (S)-1-(5-(3-fluoroisoquinolin-6-yl)-1,3,4-thiadiazol-2-ylamino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate

Product 1

HCID 86636676N-((S)-2-Amino-3-(4-(trifluoromethyl)phenyl)propyl)-5-(3-fluoroisoquinolin-6-yl)-1,3,4-thiadiazol-2-amine trifluoroacetateYield 100%

Procedure

A mixture of tert-butyl (S)-1-(5-(3-fluoroisoquinolin-6-yl)-1,3,4-thiadiazol-2-ylamino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate (0.047 g, 0.086 mmol) in TFA/DCM (1:1, 4.0 mL) was stirred at room temperature for 30 minutes. The solvent was evaporated to provide the product as an off-white solid (50.3 mg, 100%). LCMS (API-ES) m/z: 449 (M+H+); 1H NMR (400 MHz, DMSO-d6) δ ppm 3.05 (d, J=6.85 Hz, 2H), 3.54-3.65 (m, 2 H), 7.57 (d, J=8.02 Hz, 2 H), 7.72 (d, J=7.82 Hz, 3 H), 7.76 (s, 1 H), 8.03 (s, 3 H), 8.11 (dd, J=8.61, 1.57 Hz, 1 H), 8.28 (d, J=8.80 Hz, 1 H), 8.33-8.39 (m, 2 H).

Workup

customThe solvent was evaporated

Sources & evidence

ORD record: ord-ee8a0451f1a54fb6b4c1a8a67082a413
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919504B2

Reaction notes

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