Chloride → HCID 22317271, compound

HRID 498853Notes

Reaction equation

HRID 498853 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:10]=[C:11]([C:15]3[CH2:21][C:20](=[O:22])[NH:19][C:18]4[CH:23]=[C:24]([C:33]([F:36])([F:35])[F:34])[C:25]([N:27]([CH2:29][CH:30]([CH3:32])[CH3:31])[CH3:28])=[CH:26][C:17]=4[N:16]=3)[CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][N:4]=1.S(Cl)(Cl)=O.[Cl-].[CH3:42][O-].[Na+]>C(Cl)Cl.CO>[CH2:29]([N:27]([CH3:28])[C:25]1[C:24]([C:33]([F:35])([F:36])[F:34])=[CH:23][C:18]2[NH:19][C:20](=[O:22])[CH2:21][C:15]([C:11]3[CH:12]=[CH:13][CH:14]=[C:9]([C:7]4[CH:6]=[CH:5][N:4]=[C:3]([CH2:2][O:1][CH3:42])[CH:8]=4)[CH:10]=3)=[N:16][C:17]=2[CH:26]=1)[CH:30]([CH3:32])[CH3:31]

Participants

7

Reactant 4

HCID 312ChlorideHCID 24386Thionyl ChlorideHCID 10942334Sodium MethoxideHCID 22317902HCID 22317902, compound

Product 1

HCID 22317271HCID 22317271, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

The title compound was prepared from 4-[3-(2-hydroxymethyl-pyridin-4-yl)-phenyl]-7-(isobutyl-methyl-amino)-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Example 366) (248 mg, 0.50 mmol) by reaction with thionylchloride in CH2Cl2 and subsequent treatment of the corresponding crude chloride with sodium methanolate (5.4M, 1 ml) in MeOH (5 ml)/CH2Cl2 (5 ml) according to the general procedure of Example 288. Obtained as a light yellow solid (58 mg, 23%).

Sources & evidence

ORD record
ord-12c0576cf7be4d9e81b50ffea35af7a9
Source dataset
uspto-grants-2005_09
Patent number
US06949542B2

Reaction notes

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