HCID 86636502, compound → HCID 57971494, compound

HRID 913236Notes

Reaction equation

HRID 913236 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:10]([NH:20][C:21]([C:23]2[CH:40]=[CH:39][C:26]([CH2:27][NH:28]C(=O)OCC3C=CC=CC=3)=[CH:25][CH:24]=2)=[O:22])=[N:11][N:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[NH2:28][CH2:27][C:26]1[CH:25]=[CH:24][C:23]([C:21]([NH:20][C:10]2[C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:13][N:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]=2)=[O:22])=[CH:40][CH:39]=1

Participants

4

Reactant 1

HCID 86636502HCID 86636502, compound

Product 1

HCID 57971494HCID 57971494, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of benzyl {4-[({4-[(tert-butoxycarbonyl)amino]-1-phenyl-1H-pyrazol-3-yl}amino)carbonyl]benzyl}carbamate (0.75 g, 1.38 mmol) in methanol (150 mL) was treated with palladium hydroxide on carbon (75 mg) and placed under a hydrogen atmosphere for 1.5 hours. The reaction was filtered, evaporated in vacuo and purified by flash column chromatography (1-18% methanol/methylene chloride) to give title compound as an off-white solid. 1H NMR (DMSO-d6) δ 8.37 (s, 1H), 7.99 (d, J=8.2 Hz, 2H), 7.71 (d, J=7.9 Hz, 2H), 7.50 (d, J=8.2 Hz, 2H), 7.45 (t, J=7.6 Hz, 2H), 7.27 (t, J=7.3 Hz, 1H), 3.90 (s, 2H), 1.50 (s, 9H); ESIMS calcd 408.2 (M++H), found 408.1 (M++H).

Workup

  1. filtrationThe reaction was filtered
  2. customevaporated in vacuo
  3. custompurified by flash column chromatography (1-18% methanol/methylene chloride)

Sources & evidence

ORD record
ord-d5ffa4edc0ad43da8bf1c5cf937fe1a0
Source dataset
uspto-grants-2011_09
Patent number
US08026260B2

Reaction notes

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