Water → HCID 86601206, compound

HRID 349253Notes

Reaction equation

C[O:2][C:3]([C:5]1[N:6]=[N:7][N:8]([CH2:16][C:17]2[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=2)[C:9]=1[C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=O.[BH4-].[Na+].O>CO>[F:26][C:23]([F:24])([F:25])[C:21]1[CH:22]=[C:17]([CH:18]=[C:19]([C:27]([F:28])([F:30])[F:29])[CH:20]=1)[CH2:16][N:8]1[C:9]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[C:5]([CH2:3][OH:2])[N:6]=[N:7]1

Participants

Conditions

Temperature: 70 °C

Procedure

Dissolve 1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-3-yl-1H-[1,2,3]triazole-4-carboxylic acid methyl ester (10.0 g) in MeOH (110 mL). Add NaBH4 (2.64 g, 3 eq) and warm to reflux overnight (70° C.). Cool to RT and slowly pour into a separatory funnel containing an equal volume of water; extract with CH2Cl2. Dry the organic layer, concentrate, and recrystallize from EtOAc/Hexanes to give 7.0 g (75%) of the title compound. MS (ES) 403.2 (M+1); 1H NMR: (400 MHz, CD3OD) δ: 8.65 (dd, J=5.2, 1.6 Hz, 1H) 8.53–8.52 (m, 1H), 7.89 (s, 1H), 7.86–7.83 (m, 1H), 7.60 (s, 2H), 7.56–7.53 (m, 1H), 5.83 (s, 2H), 4.59 (s, 2H).

Workup

temperatureCool to RT
additionslowly pour into a separatory funnel
extractionextract with CH2Cl2
customDry the organic layer
concentrationconcentrate
customrecrystallize from EtOAc/Hexanes

Sources & evidence

ORD record: ord-9d555638b882430a9b042d2007df67eb
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179804B2

Reaction notes

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