Hydrochloric Acid → (2S,3S)-2-amino-4-hydroxy-N-(5-(isoquinolin-6-yl)-1,3,4-thiadiazol-2-yl)-3-(4-(trifluoromethyl)phenyl)butanamide hydrochloride

HRID 2075363Notes

Reaction equation

HRID 2075363 reaction equation
[Si]([O:8][CH2:9][C@@H:10]([C:38]1[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][CH:39]=1)[C@H:11]([NH:30]C(=O)OC(C)(C)C)[C:12]([NH:14][C:15]1[S:16][C:17]([C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[CH:26]=[N:25][CH:24]=[CH:23]3)=[N:18][N:19]=1)=[O:13])(C(C)(C)C)(C)C.[ClH:48]>O1CCOCC1>[ClH:48].[NH2:30][C@@H:11]([C@H:10]([C:38]1[CH:43]=[CH:42][C:41]([C:44]([F:45])([F:46])[F:47])=[CH:40][CH:39]=1)[CH2:9][OH:8])[C:12]([NH:14][C:15]1[S:16][C:17]([C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[CH:26]=[N:25][CH:24]=[CH:23]3)=[N:18][N:19]=1)=[O:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57991863HCID 57991863, compound

Product 1

HCID 67089297(2S,3S)-2-amino-4-hydroxy-N-(5-(isoquinolin-6-yl)-1,3,4-thiadiazol-2-yl)-3-(4-(trifluoromethyl)phenyl)butanamide hydrochlorideYield 12%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl (2S,3S)-4-(tert-butyldimethylsilyloxy)-1-(5-(isoquinolin-6-yl)-1,3,4-thiadiazol-2-ylamino)-1-oxo-3-(4-trifluoromethylphenyl)butan-2-ylcarbamate (0.014 g, 0.020 mmol) was taken up in 2 mL of 4 N HCl in dioxane. After 1.5 hours, a white precipitate formed. The precipitate was collected by filtration to provide (2S,3S)-2-amino-4-hydroxy-N-(5-(isoquinolin-6-yl)-1,3,4-thiadiazol-2-yl)-3-(4-(trifluoromethyl)phenyl)butanamide hydrochloride (1.2 mg, 12%). LCMS (M+H) 474 calc. for C22H19F3N5O2S 474.1. 1H NMR (400 MHz, CD3OD): δ ppm 9.84-9.78 (m 1H), 8.90-8.55 (m, 6H), 7.80-6.58 (m, 3H), 4.83-4.72 (m 2H), 4.09-3.90 (m, 1H), 3.72-3.54 (m, 1H). 4H not detected.

Workup

  1. customa white precipitate formed
  2. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-8b691fab07234b9d926118666640a93a
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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