Formic Acid → HCID 67070732, compound

HRID 273162Notes

Reaction equation

HRID 273162 reaction equation
[C:1]([BH3-])#[N:2].[Na+].[Cl:5][C:6]1[CH:7]=[C:8]([C:12]2[N:16]=[C:15]([C@@H:17](N)[CH2:18][C:19]3[N:23]([CH:24]4[CH2:26][CH2:25]4)[C:22]([C:27]4[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=4)=[N:21][N:20]=3)[O:14][N:13]=2)[CH:9]=[CH:10][CH:11]=1.[CH:34](O)=O.C=O>CO>[Cl:5][C:6]1[CH:7]=[C:8]([C:12]2[N:16]=[C:15]([C@@H:17]([N:2]([CH3:1])[CH3:34])[CH2:18][C:19]3[N:23]([CH:24]4[CH2:26][CH2:25]4)[C:22]([C:27]4[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=4)=[N:21][N:20]=3)[O:14][N:13]=2)[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67070514HCID 67070514, compound

Product 1

HCID 67070732HCID 67070732, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (0.1 mL, 1M in THF) was added to a solution of (S)-1-[3-(3-Chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-2-(4-cyclopropyl-5-pyridin-4-yl-4H-[1,2,4]triazol-3-yl)-ethylamine (30 mg) in methanol (0.8 mL) containing 96% formic acid (0.1 mL) and 37% formalin solution (0.1 mL). The residue was quenched with water and extracted with ethyl acetate. The organic layer was dried with sodium sulfate and concentrated. Purification was performed by flash column silica gel chromatography with 3% (2 M ammnonia methanol) in dichloromethane to give 22 mg of the title compound. 1H NMR (CDCl3): d ppm 8.76 (d, 2H), 8.06 (s, 1H), 7.97 (d, 1H), 7.73 (d, 2H), 7.47 (d, 1H), 7.45 (t, 1H), 5.00 (dd, 1H), 3.76 (dd, 1H), 3.51 (dd, 1H), 3.42 (m, 1H), 2.45 (br s, 6H), 1.26 (m, 2H), 0.88 (m, 1H), 0.79 (m, 1H)

Workup

  1. customThe residue was quenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. concentrationconcentrated
  5. customPurification

Sources & evidence

ORD record
ord-f130a1debd494d56a13e8415e8476cf4
Source dataset
uspto-grants-2008_11
Patent number
US07456200B2

Reaction notes

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