Pyrazole → (r)-4-Bromo-5-(2-chlorobenzoylamino)-1-methyl-pyrazole-3-carboxylic acid (1,5-dimethyl-2-oxo-2,3,4,5-tetrahydro-1h-benzo[b][1,4]diazepin-3-yl)amide

HRID 2114308Notes

Reaction equation

HRID 2114308 reaction equation
N1C=C[CH:3]=N1.[CH3:6][N:7]([C@@H:26]([C:28]1C=CC=C[CH:29]=1)C)[C:8](C1C(Br)=C(NC(=O)C2C=CC=CC=2Cl)NN=1)=[O:9].[Cl:34][C:35]1[CH:43]=[CH:42][CH:41]=[CH:40][C:36]=1[C:37](Cl)=[O:38].[N:44]1([CH2:49][CH2:50][NH:51][C:52]([C:54]2[C:58]([Br:59])=[C:57]([NH:60]C(=O)C3C=CC=CC=3Cl)[NH:56][N:55]=2)=[O:53])[CH2:48][CH2:47][CH2:46][CH2:45]1>>[CH3:6][N:7]1[C:8](=[O:9])[C@H:50]([NH:51][C:52]([C:54]2[C:58]([Br:59])=[C:57]([NH:60][C:37](=[O:38])[C:36]3[CH:40]=[CH:41][CH:42]=[CH:43][C:35]=3[Cl:34])[N:56]([CH3:3])[N:55]=2)=[O:53])[CH2:49][N:44]([CH3:45])[C:48]2[CH:47]=[CH:46][CH:29]=[CH:28][C:26]1=2

Participants

5

Reactant 4

HCID 1048PyrazoleHCID 691102-Chlorobenzoyl chlorideHCID 178461679HCID 178461679, compoundHCID 178522629HCID 178522629, compound

Product 1

HCID 59773391(r)-4-Bromo-5-(2-chlorobenzoylamino)-1-methyl-pyrazole-3-carboxylic acid (1,5-dimethyl-2-oxo-2,3,4,5-tetrahydro-1h-benzo[b][1,4]diazepin-3-yl)amide

Procedure

The pyrazole acid, prepared by coupling methyl ester 85 (Gen. Proc. 26) with 2-chlorobenzoyl chloride (21) followed by hydrolysis and bromination as shown in Gen. Proc. 8. was coupled to compound 92 (Procedure 27) using the method of Procedure 3.

Workup

  1. customfollowed by hydrolysis and bromination

Sources & evidence

ORD record
ord-f916f3bd86ef43c9848028e3ab5e0dd9
Source dataset
uspto-grants-2008_10
Patent number
US07432379B2

Reaction notes

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