Morpholine → HCID 10476568, compound

HRID 222704Notes

Reaction equation

HRID 222704 reaction equation
[CH:1]1([N:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][C:14]([O:16][C:17]4[CH:18]=[N:19][C:20]([C:23](O)=[O:24])=[N:21][CH:22]=4)=[CH:15][C:8]=3[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1>CN(C)C=O>[CH:1]1([N:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][C:14]([O:16][C:17]4[CH:18]=[N:19][C:20]([C:23]([N:38]5[CH2:43][CH2:42][O:41][CH2:40][CH2:39]5)=[O:24])=[N:21][CH:22]=4)=[CH:15][C:8]=3[CH2:7][CH2:6]2)[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 9974449HCID 9974449, compound

Product 1

HCID 10476568HCID 10476568, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-[(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-2-pyrimidinecarboxylic acid (E177b) (130 mg, 0.37 mmol) was dissolved in dimethylformamide (4 ml), treated with 1,1′-carbonyldiimidazole (180 mg, 1.11 mmol) and left to stir under argon at room temperature for 5 hours. The mixture was treated with morpholine (0.19 ml, 2.22 mmol) and allowed to stir at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the resulting residue purified by column chromatography eluting with a mixture of 0.880 ammonia:methanol:dichloromethane (0.5:1.5:95) to afford the title compound (E177). MS (ES+) m/e 409 [M+H]+.

Workup

  1. waitleft
  2. stirringto stir at room temperature for 18 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe resulting residue purified by column chromatography
  5. washeluting with a mixture of 0.880 ammonia:methanol:dichloromethane (0.5:1.5:95)

Sources & evidence

ORD record
ord-3e9265e051e04853a6345e4f5ad78f92
Source dataset
uspto-grants-2012_06
Patent number
US08207331B2

Reaction notes

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