Dimethylamine → 1,1-Dimethylethyl 2-{4-[(dimethylamino)carbonyl]phenyl}-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine-6(2H)-carboxylate

HRID 1364132Notes

Reaction equation

HRID 1364132 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2=[CH:15][N:16]([C:18]3[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][CH:19]=3)[N:17]=[C:11]2[CH2:10][CH2:9]1)=[O:7])([CH3:4])[CH3:3].O=[C:28](N1C=CN=C1)[N:29]1C=CN=[CH:30]1.CNC>ClCCl.O>[CH3:28][N:29]([CH3:30])[C:22]([C:21]1[CH:25]=[CH:26][C:18]([N:16]2[CH:15]=[C:12]3[C:11]([CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:3])([CH3:1])[CH3:4])=[O:7])[CH2:14][CH2:13]3)=[N:17]2)=[CH:19][CH:20]=1)=[O:24]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 669308134-[6-{[(1,1-dimethylethyl)oxy]carbonyl}-5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl]benzoic acid

Product 1

HCID 669309031,1-Dimethylethyl 2-{4-[(dimethylamino)carbonyl]phenyl}-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine-6(2H)-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-[6-{[(1,1-dimethylethyl)oxy]carbonyl}-5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl]benzoic acid (may be prepared as described in Description 23) (185 mg, 0.52 mmol) in dichloromethane (10 ml) was added 1,1′-(oxomethanediyl)bis-1H-imidazole (168 mg, 1.04 mmol) and the reaction stirred at room temperature, under argon, overnight. Dimethylamine (93 mg, 2.07 mmol) was added and stirring continued, under argon, at room temperature for 4 hours. The resulting crude mixture was diluted with water, and extracted with dichloromethane (×2). The combined organic fractions were washed with water (×1), dried over magnesium sulphate and solvent evaporated in vacuo to afford the title compound (D41). MS (ES+) m/e 385 [M+H]+.

Workup

  1. stirringstirring continued, under argon, at room temperature for 4 hours
  2. extractionextracted with dichloromethane (×2)
  3. washThe combined organic fractions were washed with water (×1)
  4. dry with materialdried over magnesium sulphate and solvent
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-a564fa8cfc0e44a7a02257b7205e2f3f
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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