Trifluoroacetic acid methylene chloride → HCID 57991855, compound

HRID 2075366Notes

Reaction equation

HRID 2075366 reaction equation
C(O)(C(F)(F)F)=O.C(Cl)Cl.[CH:11]1[C:20]2[C:15](=[CH:16][C:17]([C:21]3[S:25][C:24]([O:26][CH2:27][C@@H:28]([NH:40]C(=O)OC(C)(C)C)[CH2:29][C:30]4[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=4)=[N:23][N:22]=3)=[CH:18][CH:19]=2)[CH:14]=[CH:13][N:12]=1>>[CH:11]1[C:20]2[C:15](=[CH:16][C:17]([C:21]3[S:25][C:24]([O:26][CH2:27][C@@H:28]([NH2:40])[CH2:29][C:30]4[CH:31]=[CH:32][C:33]([C:36]([F:37])([F:39])[F:38])=[CH:34][CH:35]=4)=[N:23][N:22]=3)=[CH:18][CH:19]=2)[CH:14]=[CH:13][N:12]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 57991959HCID 57991959, compound

Product 1

HCID 57991855HCID 57991855, compoundYield 42%

Procedure

A 50% TFA/DCM mixture (2 mL) was added to tert-butyl (S)-1-(5-(isoquinolin-6-yl)-1,3,4-thiadiazol-2-yloxy)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate. After 30 minutes, the reaction mixture was concentrated. The residue was purified by reverse phase C-18 HPLC chromatography to provide (2S)-1-(5-(isoquinolin-6-yl)-1,3,4-thiadiazol-2-yloxy)-3-(4-(trifluoromethyl)phenyl)propan-2-amine (50 mg, 42% over two steps). LCMS 431 (M+H) calc. for C21H18F3N4OS 431.1. 1H NMR (400 MHz, CDCl3): δ ppm 3.14 (d, J=6.46 Hz, 2H) 3.81-3.88 (m, 2H) 3.95-4.00 (m, 1H) 7.43 (d, J=8.02 Hz, 2H) 7.60 (d, J=8.22 Hz, 2H) 8.03 (d, J=6.26 Hz, 1H) 8.17 (s, 1H) 8.22-8.28 (m, 2H) 8.62 (d, J=6.26 Hz, 1H) 9.58 (s, 1H). 2H not detected.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customThe residue was purified by reverse phase C-18 HPLC chromatography

Sources & evidence

ORD record
ord-beaeb6b9d3694cc8868158072fc5a1ac
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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