HCID 66665648, compound → HCID 66665191, compound

HRID 872352Notes

Reaction equation

HRID 872352 reaction equation
[NH2:1][C:2]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:13]=[C:14]4[CH:19]=[C:18](/[CH:20]=[CH:21]/[C:22]([NH2:24])=[O:23])[CH:17]=[CH:16][N:15]4[C:25]=3[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3]1>[Pd].CO>[NH2:1][C:2]1([C:6]2[CH:7]=[CH:8][C:9]([C:12]3[N:13]=[C:14]4[CH:19]=[C:18]([CH2:20][CH2:21][C:22]([NH2:24])=[O:23])[CH:17]=[CH:16][N:15]4[C:25]=3[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:10][CH:11]=2)[CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 66665648HCID 66665648, compound

Product 1

HCID 66665191HCID 66665191, compoundYield 21.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

A mixture of (E)-3-{2-[4-(1-amino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyridin-7-yl}-acrylamide (111 mg, 0.27 mmol) and 10% palladium on carbon (14 mg) in MeOH (10 mL) was stirred under a hydrogen atmosphere for 23 h, additional palladium on carbon (14 mg) was added and the reaction was stirred under a hydrogen atmosphere for 6 h. The resulting mixture was filtered. The resulting solution was concentrated under reduced pressure. The remaining material was purified using MPLC (Biotage Isolera Flash NH2 Snap 10 reverse phase column; 100% CH2Cl2 for 8 min., gradient to 95% CH2Cl2: 5% MeOH over 5 min.; 95% CH2Cl2: 5% MeOH for 4 min., gradient to 80% CH2Cl2: 20% MeOH over 5 min., 80% CH2Cl2: 20% MeOH for 6.2 min.) to give 3-{2-[4-(1-amino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyridin-7-yl}-propionamide (24 mg, 17%):

Workup

  1. stirringthe reaction was stirred under a hydrogen atmosphere for 6 h
  2. filtrationThe resulting mixture was filtered
  3. concentrationThe resulting solution was concentrated under reduced pressure
  4. customThe remaining material was purified
  5. wait100% CH2Cl2 for 8 min.
  6. waitgradient to 95% CH2Cl2: 5% MeOH over 5 min.
  7. wait95% CH2Cl2: 5% MeOH for 4 min.
  8. waitgradient to 80% CH2Cl2: 20% MeOH over 5 min.

Sources & evidence

ORD record
ord-a5791e99e8e5475995073f000c50fc7f
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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