3-Hydroxybenzoic Acid → (3RS)-1-(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl-2,3-dihydro-3-(3-hydroxyphenyl)carbonylamino-5-(2-fluorophenyl)-1H-1,4-benzodiazepin-2-one

HRID 963523

Reaction equation

HRID 963523 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]=[CH:19][C:5]=2[N:4]([CH2:20][C:21]([N:23]2[CH2:29][CH:28]3[CH2:30][CH2:31][CH:25]([CH2:26][CH2:27]3)[CH2:24]2)=[O:22])[C:3]1=[O:32].[OH:33][C:34]1[CH:35]=[C:36]([CH:40]=[CH:41][CH:42]=1)[C:37](O)=[O:38].CCN=C=NCCCN(C)C.Cl.C(OCC)(=O)C>C(Cl)Cl.Cl>[CH:25]12[CH2:31][CH2:30][CH:28]([CH2:27][CH2:26]1)[CH2:29][N:23]([C:21]([CH2:20][N:4]1[C:5]3[CH:19]=[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:37]([C:36]3[CH:40]=[CH:41][CH:42]=[C:34]([OH:33])[CH:35]=3)=[O:38])[C:3]1=[O:32])=[O:22])[CH2:24]2

Participants

7

Reactant 4

HCID 74203-Hydroxybenzoic AcidHCID 8857Ethyl AcetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19081160(3RS)-1-{(3-azabicyclo[3.2.2]non-3-yl)-carbonylmethyl}-3-amino-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one

Product 1

HCID 19081329(3RS)-1-(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl-2,3-dihydro-3-(3-hydroxyphenyl)carbonylamino-5-(2-fluorophenyl)-1H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (3RS)-3-amino-1-[(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl]-2,3-dihydro-5-(2-fluorophenyl)-1H-1,4-benzodiazepin-2-one, 3-hydroxybenzoic acid, and WSC-HCl was stirred in CH2Cl2 at room temperature overnight. Ethyl acetate and iN HCl were added in the reaction mixture and organic layer was separated, and washed with water and brine, and dried over magnesium sulfate, evaporated in vacuo. The colorless powder was washed with isopropyl ether to afford (3RS)-1-(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl-2,3-dihydro-3-(3-hydroxyphenyl)carbonylamino-5-(2-fluorophenyl)-1H-1,4-benzodiazepin-2-one.

Workup

  1. customwas separated
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. washThe colorless powder was washed with isopropyl ether

Sources & evidence

ORD record
ord-5993912ac1ae49a68d979e7d042c8af3
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Linked notes

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