1,1'-Carbonyldiimidazole → HCID 70981308, compound

HRID 1749107Notes

Reaction equation

HRID 1749107 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[C:13]([O:17][C:18](=[O:46])[N:19]([C:31]1[CH:36]=[CH:35][C:34]([NH2:37])=[C:33]([CH2:38][NH:39][CH:40]2[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]2)[N:32]=1)[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=1[O:29][CH3:30])([CH3:16])([CH3:15])[CH3:14]>C1COCC1>[C:13]([O:17][C:18](=[O:46])[N:19]([C:31]1[CH:36]=[CH:35][C:34]2[NH:37][C:1](=[O:2])[N:39]([CH:40]3[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]3)[CH2:38][C:33]=2[N:32]=1)[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=1[O:29][CH3:30])([CH3:16])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 70979874HCID 70979874, compound

Product 1

HCID 70981308HCID 70981308, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1,1′-carbonyldiimidazole (162 mg, 1.0 mmol, 1.2 equiv) in THF (5 mL) was added a solution of (5-amino-6-cyclohexylaminomethyl-pyridin-2-yl)-(2,4-dimethoxy-benzyl)-carbamic acid tert-butyl ester (390 mg, 0.83 mmol, 1.0 equiv) in THF (5 mL) and the reaction mixture was stirred for 2 h. The solvent was evaporated, the residue was dissolved in EtOAc, washed with water, brine, dried (MgSO4), filtered and the solvent was evaporated. The residue was crystallized from methanol to afford (3-cyclohexyl-2-oxo-1,2,3,4-tetrahydro-pyrido[3,2-d]pyrimidin-6-yl)-(2,4-dimethoxy-benzyl)-carbamic acid tert-butyl ester (282 mg) as a white solid. MS: [M+H]+=496.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-860d26569ae74c3b93ccfb6f95c150b4
Source dataset
uspto-grants-2015_10
Patent number
US09155743B2

Reaction notes

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