Cyclopropanemethanamine → HCID 73387065, compound

HRID 1480786Notes

Reaction equation

HRID 1480786 reaction equation
Cl[C:2]1[C:7]2[N:8]=[C:9]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=4)=[CH:15][C:14]=3[CH3:25])[N:10]=[CH:11][C:6]=2[CH:5]=[CH:4][N:3]=1.[CH:26]1([CH2:29][NH2:30])[CH2:28][CH2:27]1>CN1C(=O)CCC1.C([O-])(O)=O.[Na+].CCOC(C)=O>[CH:26]1([CH2:29][NH:30][C:2]2[C:7]3[N:8]=[C:9]([NH:12][C:13]4[CH:18]=[CH:17][C:16]([C:19]5[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=5)=[CH:15][C:14]=4[CH3:25])[N:10]=[CH:11][C:6]=3[CH:5]=[CH:4][N:3]=2)[CH2:28][CH2:27]1

Participants

6

Reactant 2

HCID 75646CyclopropanemethanamineHCID 89996303HCID 89996303, compound

Product 1

HCID 73387065HCID 73387065, compoundYield 10%

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 8-chloro-N-(2-methyl-4-(1-methyl-1H-pyrazol-4-yl)phenyl)pyrido[3,4-d]pyrimidin-2-amine (Preparation 113, 40 mg, 0.114 mmol) in NMP (3 mL) was added cyclopropanemethylamine (0.1 ml, 1.140 mmol). The reaction mixture was heated to 120° C. for 18 hours. The reaction mixture was diluted with aqueous saturated NaHCO3 (20 mL) and EtOAc (2×20 mL). The combined organic layers were washed with water (30 mL) and brine (30 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 0-5% MeOH in EtOAc to give the title compound (4.2 mg, 10%).

Workup

  1. washThe combined organic layers were washed with water (30 mL) and brine (30 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography
  5. washeluting with 0-5% MeOH in EtOAc

Sources & evidence

ORD record
ord-fb8b1aee405343ca82ba1fc5cd7e7b11
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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