HCID 59596400, compound → HCID 59596404, compound

HRID 2264584Notes

Reaction equation

HRID 2264584 reaction equation
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([NH:17][C:18]([N:20]2[CH2:26][CH2:25][CH2:24][CH2:23][C:22]3[CH:27]=[C:28]([O:31][C:32]4[CH:37]=[C:36](Cl)[N:35]=[C:34]([NH2:39])[N:33]=4)[CH:29]=[CH:30][C:21]2=3)=[O:19])[CH:6]=[CH:7][C:8]=1[CH2:9][N:10]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]1>CO.[Pd]>[F:41][C:2]([F:1])([F:40])[C:3]1[CH:4]=[C:5]([NH:17][C:18]([N:20]2[CH2:26][CH2:25][CH2:24][CH2:23][C:22]3[CH:27]=[C:28]([O:31][C:32]4[CH:37]=[CH:36][N:35]=[C:34]([NH2:39])[N:33]=4)[CH:29]=[CH:30][C:21]2=3)=[O:19])[CH:6]=[CH:7][C:8]=1[CH2:9][N:10]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]1

Participants

4

Reactant 1

HCID 59596400HCID 59596400, compound

Product 1

HCID 59596404HCID 59596404, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

250 mg (0.42 mMol) of 7-(2-amino-6-chloro-pyrimidin-4-yloxy)-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid [3-trifluoromethyl-4-(4-methylpiperazin-1-ylmethyl)-phenyl]-amide in 35 ml methanol are hydrogenated in the presence of 160 mg Pd/C (10%; Engelhard 4505). The catalyst is filtered off, the filtrate diluted with EtOAc and sat. Na2CO3/H2O 1:1 and the separated aqueous layer extracted twice with water. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Reversed phase MPLC (Gilson system) gives the title compound: MS: [M+1]+=556; HPLC: AtRet=9.0.

Workup

  1. filtrationThe catalyst is filtered off
  2. additionthe filtrate diluted with EtOAc and sat. Na2CO3/H2O 1:1
  3. extractionthe separated aqueous layer extracted twice with water
  4. washThe organic layers are washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b8c7a00f185c4cd382a0e639176eada3
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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