Hydrochloric Acid → 3-Amino-1-(3-(trifluoromethyl)-5,6-dihydro(1,2,4)triazolo(4,3-a)pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one

HRID 870319Notes

Reaction equation

[O:1]=[C:2]([N:16]1[CH2:21][CH2:20][N:19]2[C:22]([C:25]([F:28])([F:27])[F:26])=[N:23][N:24]=[C:18]2[CH2:17]1)[CH:3]=[C:4]([NH2:15])[CH2:5][C:6]1[CH:11]=[C:10]([F:12])[C:9]([F:13])=[CH:8][C:7]=1[F:14].C([BH3-])#N.[Na+].Cl>CO>[O:1]=[C:2]([N:16]1[CH2:21][CH2:20][N:19]2[C:22]([C:25]([F:28])([F:27])[F:26])=[N:23][N:24]=[C:18]2[CH2:17]1)[CH2:3][CH:4]([NH2:15])[CH2:5][C:6]1[CH:11]=[C:10]([F:12])[C:9]([F:13])=[CH:8][C:7]=1[F:14]

Participants

Conditions

Temperature: 30 °C

Procedure

A mixture of methanol (135 ml), 7-(1-oxo-3-amino-4-(2,4,5-trifluorophenyl)-but-2-enyl)-3-trifluoromethyl-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyrazine (13.5 gm), sodium cyano borohydride (2.5 g), and methanolic hydrogen chloride (35 mL) at about 4.5 pH is stirred for about 5 hours at about 30° C. The solvent is distilled off completely and water (50 mL) is added to the residue. The extraction is carried out with ethylacetate (150 mL). The obtained organic layer is distilled off completely to afford the title compound. (Yield: 99.9%; purity by HPLC: 92.25%)

Workup

distillationThe solvent is distilled off completely
additionwater (50 mL) is added to the residue
extractionThe extraction
distillationThe obtained organic layer is distilled off completely

Sources & evidence

ORD record: ord-0533415ca1a649a7a0b2143f1b34d01a
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969558B2

Reaction notes

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