Pyrazole → (r)-4-Bromo-5-(2-chloro-benzoylamino)-1-methyl-pyrazole-3-carboxylic acid (azepan-3-yl)-amide

HRID 2114311Notes

Reaction equation

HRID 2114311 reaction equation
N1C=C[CH:3]=N1.CN([C@@H](C1C=CC=CC=1)C)C([C:10]1[C:14]([Br:15])=[C:13]([NH:16][C:17](=[O:25])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[NH:12][N:11]=1)=O.ClC1C=CC=CC=1C(Cl)=O.C(OC([N:54]1[CH2:60][CH2:59][CH2:58][CH2:57][C@@H:56]([NH:61][C:62]([O:64]C(C)(C)C)=O)[CH2:55]1)=O)C1C=CC=CC=1.N(C(OC(C)(C)C)=O)[C@@H](C(O)=O)CCCCN.N1(N)CCCCC1>>[NH:54]1[CH2:60][CH2:59][CH2:58][CH2:57][C@@H:56]([NH:61][C:62]([C:10]2[C:14]([Br:15])=[C:13]([NH:16][C:17](=[O:25])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[N:12]([CH3:3])[N:11]=2)=[O:64])[CH2:55]1

Participants

7

Reactant 6

HCID 1048PyrazoleHCID 166581-AminopiperidineHCID 691102-Chlorobenzoyl chlorideHCID 7018770Boc-D-Lys-OHHCID 69152935Benzyl (R)-3-((tert-butoxycarbonyl)amino)azepane-1-carboxylateHCID 178461679HCID 178461679, compound

Product 1

HCID 59773409(r)-4-Bromo-5-(2-chloro-benzoylamino)-1-methyl-pyrazole-3-carboxylic acid (azepan-3-yl)-amide

Procedure

The pyrazole acid, prepared by coupling methyl ester 85 (Procedure 26) with 2-chlorobenzoyl chloride (21) followed by hydrolysis and bromination as shown in Procedure 8, was coupled to (R)-3-tert-butoxycarbonylaminoazepane-1-carboxylic acid benzyl ester (prepared as described in Procedure 23 using Boc-D-Lys-OH (Bachem, A-2705) followed by Cbz protection of the piperidine amine using the method of Procedure 30) using Procedure 3. Removal of the Cbz group using the method of Procedure 20 afforded the title compound.

Workup

  1. customfollowed by hydrolysis and bromination
  2. customprepared
  3. customRemoval of the Cbz group

Sources & evidence

ORD record
ord-068b87414bc64e778bb2510284b30118
Source dataset
uspto-grants-2008_10
Patent number
US07432379B2

Reaction notes

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