Formic Acid → HCID 75202918, compound

HRID 1519133Notes

Reaction equation

HRID 1519133 reaction equation
C([N:8]1[C:12]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[CH2:21][OH:22])=[CH:11][N:10]=[N:9]1)C1C=CC=CC=1.C(O)=O>CO.[Pd]>[N:10]1[NH:9][N:8]=[C:12]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[CH2:21][OH:22])[CH:11]=1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 86724054HCID 86724054, compound

Product 1

HCID 75202918HCID 75202918, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of [2-[(3-benzyltriazol-4-yl)amino]-5-chloro-phenyl]methanol 7a (300 mg, 0.95 mmol) in MeOH (5 mL) was treated with formic acid (1.00 mL, 26.51 mmol). The mixture was degassed by vacuum/nitrogen cycles before the addition of palladium on carbon (507.1 mg, 0.48 mmol). The mixture was stirred under an argon atmosphere at room temperature for 18 h and then filtered through celite and concentrated. The material was purified by FractionLynx to afford the title compound I-9 as a solid (90.0 mg, 40%). 1H NMR (500 MHz, DMSO) δ 14.20 (1H, s), 7.85-7.80 (1H, s), 7.60 (1H, s), 7.51 (1H, s), 7.31 (1H, d), 7.19 (1H, d), 4.55 (2H, s). MS m/z: 223.1 (M−H)+.

Workup

  1. filtrationfiltered through celite
  2. concentrationconcentrated
  3. customThe material was purified by FractionLynx

Sources & evidence

ORD record
ord-2b77056f2a9d4e5498f53a58ce6712ae
Source dataset
uspto-grants-2015_07
Patent number
US09073875B2

Reaction notes

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