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

HRID 2114311노트

반응식

HRID 2114311 반응식
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

참가 물질

7

반응물 6

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

생성물 1

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

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-068b87414bc64e778bb2510284b30118
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432379B2

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