Dichloromethane → HCID 67423402, compound

HRID 1930688Notes

Reaction equation

HRID 1930688 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([CH:12]2[C:17](=O)[CH2:16][CH2:15][N:14]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:13]2)=O)[CH:6]=[CH:7][CH:8]=1.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[CH3:34][O:35][C:36]1[CH:37]=[C:38]([NH:48][C:49]([NH2:51])=[NH:50])[CH:39]=[CH:40][C:41]=1[N:42]1[CH:46]=[C:45]([CH3:47])[N:44]=[CH:43]1.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>C(O)C.O>[CH3:34][O:35][C:36]1[CH:37]=[C:38]([NH:48][C:49]2[N:51]=[C:10]([CH2:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[C:12]3[CH2:13][N:14]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:16][C:17]=3[N:50]=2)[CH:39]=[CH:40][C:41]=1[N:42]1[CH:46]=[C:45]([CH3:47])[N:44]=[CH:43]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 59333808HCID 59333808, compoundHCID 178493228HCID 178493228, compound

Product 1

HCID 67423402HCID 67423402, compoundYield 3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

tert-Butyl 3-(2-(3-methoxyphenyl)acetyl)-4-oxopiperidine-1-carboxylate (320 mg, 0.92 mmol), 1-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)guanidine dinitrate (342 mg, 0.92 mmol, example 43a) and potassium carbonate (382 mg, 2.76 mmol) in ethanol (4 mL) was heated in a microwave reactor to 130° C. for 3 hours. DCM and water was added and the organic phases were separated, dried with MgSO4, concentrated and purified by preparative HPLC to afford tert-butyl 2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-4-(3-methoxybenzyl)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (15.00 mg, 3%).

Workup

  1. customthe organic phases were separated
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-baaa7dcffed747bb88c15d29d8058fad
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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