Ammonium Chloride → HCID 45110549, compound

HRID 445983Notes

Reaction equation

[Na].[O:2]=[C:3]([N:17]1[CH2:22][CH2:21][N:20]2[C:23]([C:26]([F:29])([F:28])[F:27])=[N:24][N:25]=[C:19]2[CH2:18]1)[CH2:4][C:5](=[O:16])[CH2:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([F:14])=[CH:9][C:8]=1[F:15].[BH4-].[Na+].[NH4+].[Cl-]>CO.C1COCC1>[OH:16][CH:5]([CH2:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([F:14])=[CH:9][C:8]=1[F:15])[CH2:4][C:3]([N:17]1[CH2:22][CH2:21][N:20]2[C:23]([C:26]([F:29])([F:28])[F:27])=[N:24][N:25]=[C:19]2[CH2:18]1)=[O:2]

Participants

Conditions

Temperature: -4 °C

Procedure

In a 500 mL round bottom flask THF (50 mL) and methanol (100 mL) were taken. To the solution sodium salt of 4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-one (2.0 g) was added. It was cooled to −78 to 70° C. in a dry-ice bath. Then NaBH4 (0.7 g) was added in small lots in 10-15 min. It was stirred at −78 to 70° C. for 3-4 h. Reaction mixture was poured into aq. saturated NH4Cl solution at 0-5° C. Product was extracted with ethyl acetate. Organic layer was collected and dried over anhydrous sodium sulfate. Solvent was evaporated at reduced pressure to obtain the product. (Wt.-2.0 g, % Y-100%, % Purity by HPLC-95.6%).

Workup

customReaction mixture
extractionProduct was extracted with ethyl acetate
customOrganic layer was collected
dry with materialdried over anhydrous sodium sulfate
customSolvent was evaporated at reduced pressure
customto obtain the product

Sources & evidence

ORD record: ord-71e24d0cb89d40ce949d2620adc4e7f4
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476437B2

Reaction notes

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