1-Hydroxybenzotriazole → Rac-2-[4-(4-bromophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1h-imidazol-1-yl]-n-{1-[3-(trifluoromethyl)phenyl]ethyl}acetamide

HRID 660935노트

반응식

HRID 660935 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:18]3[CH2:20][CH2:19]3)[C:10](=[O:17])[N:11]([CH2:13][C:14]([OH:16])=O)[CH:12]=2)=[CH:4][CH:3]=1.[F:21][C:22]([F:33])([F:32])[C:23]1[CH:24]=[C:25]([CH:29]([NH2:31])[CH3:30])[CH:26]=[CH:27][CH:28]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C)C=O.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([CH:18]3[CH2:20][CH2:19]3)[C:10](=[O:17])[N:11]([CH2:13][C:14]([NH:31][CH:29]([C:25]3[CH:26]=[CH:27][CH:28]=[C:23]([C:22]([F:21])([F:32])[F:33])[CH:24]=3)[CH3:30])=[O:16])[CH:12]=2)=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2782448(1R)-1-(3-(Trifluoromethyl)phenyl)ethylamineHCID 58011674[4-(4-bromophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetic acid

생성물 1

HCID 58011855Rac-2-[4-(4-bromophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1h-imidazol-1-yl]-n-{1-[3-(trifluoromethyl)phenyl]ethyl}acetamide

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

40.0 mg (0.119 mmol) of 4-(4-bromophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetic acid from Example 129A, 24.7 mg (0.130 mmol) of 1-[3-(trifluoromethyl)phenyl]ethylamine and 19.2 mg (0.142 mmol) of HOBt are placed in 1.5 ml of dimethylformamide and treated with 29.6 mg (0.154 mmol) of EDC hydrochloride. This is stirred overnight at room temperature, then stirred with 15 ml of water, and the resulting precipitate is isolated and this crude product purified by preparative HPLC [Method 13]. 23 mg (38% of theory) of the target compound are thus obtained.

후처리

  1. customthe resulting precipitate is isolated
  2. customthis crude product purified by preparative HPLC [Method 13]
  3. custom23 mg (38% of theory) of the target compound are thus obtained

출처 및 근거

ORD 기록
ord-6bc37fe3821743df9b9adbe5f3f215a4
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084481B2

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