Water → HCID 70126426, compound

HRID 1596349Notes

Reaction equation

HRID 1596349 reaction equation
[NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])[C:6]2[CH:16]=[CH:17][CH:18]=[C:19]([CH3:20])[C:5]=2[N:4]([CH2:21][C:22]([N:24]2[CH2:30][CH:29]3[CH2:31][CH2:32][CH:26]([CH2:27][CH2:28]3)[CH2:25]2)=[O:23])[C:3]1=[O:33].[C:34](N1C=CN=C1)([N:36]1[CH:40]=[CH:39][N:38]=[CH:37]1)=[O:35].C(OCC)(=O)C.O>O1CCCC1>[CH:26]12[CH2:32][CH2:31][CH:29]([CH2:28][CH2:27]1)[CH2:30][N:24]([C:22]([CH2:21][N:4]1[C:5]3[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:6]=3[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[F:15])=[N:8][CH:2]([NH:1][C:34]([N:36]3[CH:40]=[CH:39][N:38]=[CH:37]3)=[O:35])[C:3]1=[O:33])=[O:23])[CH2:25]2

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 682631,1'-CarbonyldiimidazoleHCID 53705307HCID 53705307, compound

Product 1

HCID 70126426HCID 70126426, compoundYield 105%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (3RS)-3-amino-1-[(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl]-2,3-dihydro-9-methyl-5-(2-fluorophenyl)-1H-1,4-benzodiazepin-2-one (1.0 g) and 1,1′-carbonyldiimidazole (723 mg) in tetrahydrofuran (20 ml) was stirred at room temperature overnight. Ethyl acetate and water were added to the reaction mixture. The separated organic layer was washed with water twice, brine and dried over magnesium sulfate. The solvent was evaporated in vacuo to afford (3RS)-1-[(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl]-2,3-dihydro-5-(2-fluorophenyl)-9-methyl-3-(imidazol-1-yl)carbonylamino-1H-1,4-benzodiazepin-2-one (1.27 g) as a crystalline powder.

Workup

  1. washThe separated organic layer was washed with water twice
  2. dry with materialbrine and dried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-82a82d4f39034e47987fdb29e8314d80
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

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