Benzyl 4-{2-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl}-1-methyl-1H-pyrrole-2-carboxylate → HCID 59402268, compound

HRID 2090401Notes

Reaction equation

HRID 2090401 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH:17]([CH3:18])[CH2:16][C:15]3[C:10](=[CH:11][C:12]([C:19]4[CH:20]=[C:21]([C:25]([O:27]CC5C=CC=CC=5)=[O:26])[N:22]([CH3:24])[CH:23]=4)=[CH:13][CH:14]=3)[CH2:9]2)[CH:5]=[C:4]([N:35]2[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]2)[N:3]=1>CO.[Pd]>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH:17]([CH3:18])[CH2:16][C:15]3[C:10](=[CH:11][C:12]([C:19]4[CH:20]=[C:21]([C:25]([OH:27])=[O:26])[N:22]([CH3:24])[CH:23]=4)=[CH:13][CH:14]=3)[CH2:9]2)[CH:5]=[C:4]([N:35]2[CH2:36][CH2:37][N:38]([CH3:41])[CH2:39][CH2:40]2)[N:3]=1

Participants

4

Reactant 1

HCID 59402315Benzyl 4-{2-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl}-1-methyl-1H-pyrrole-2-carboxylate

Product 1

HCID 59402268HCID 59402268, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd/C (25.0 mg, 10 wt. % loading dry basis, matrix activated carbon, wet support, Degussa type E101 NE/W) was added to a solution of benzyl 4-{2-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl}-1-methyl-1H-pyrrole-2-carboxylate (0.10 g, 0.18 mmol) in methanol (2.0 mL) and then the reaction was stirred under hydrogen (balloon) for 2 h. LCMS showed the reaction was complete. The reaction mixture was filtered. The solvent was removed under reduced pressure to give the product which was directly used in the next step reaction without further purification. LCMS (M+H)+: m/z=462.3.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customThe solvent was removed under reduced pressure
  3. customto give the product which
  4. customwas directly used in the next step reaction without further purification

Sources & evidence

ORD record
ord-7b9e1059193244aca1754eb2fb876cb3
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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