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Triethylamine → {3-[[(3-Benzyl-5-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl) cyclopropyl-methyl]-(4-chloro-benzoyl)-amino]-propyl}-carbamic acid tert-butyl ester

HRID 1795981
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HRID 1795981 반응식
[C:1]([O:5][C:6](=[O:34])[NH:7][CH2:8][CH2:9][CH2:10][NH:11][CH:12]([C:16]1[N:21]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20](=[O:29])[C:19]2=[C:30]([Cl:33])[CH:31]=[CH:32][N:18]2[N:17]=1)[CH:13]1[CH2:15][CH2:14]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:42][C:43]1[CH:51]=[CH:50][C:46]([C:47](Cl)=[O:48])=[CH:45][CH:44]=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:34])[NH:7][CH2:8][CH2:9][CH2:10][N:11]([CH:12]([C:16]1[N:21]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20](=[O:29])[C:19]2=[C:30]([Cl:33])[CH:31]=[CH:32][N:18]2[N:17]=1)[CH:13]1[CH2:14][CH2:15]1)[C:47](=[O:48])[C:46]1[CH:50]=[CH:51][C:43]([Cl:42])=[CH:44][CH:45]=1)([CH3:4])([CH3:2])[CH3:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 69591847(3-{[(3-Benzyl-5-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-cyclopropyl-methyl]-amino}-propyl)-carbamic acid tert-butyl ester

생성물 1

HCID 69591786{3-[[(3-Benzyl-5-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl) cyclopropyl-methyl]-(4-chloro-benzoyl)-amino]-propyl}-carbamic acid tert-butyl ester수율 38.8%

시약·촉매·용매

1
HCID 6344Dichloromethane용매2회

실험 절차

(±)-(3-{[(3-Benzyl-5-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-cyclopropyl-methyl]-amino}-propyl)-carbamic acid tert-butyl ester (Example 22H, 16 mg, 0.033 mmol) in methylene chloride (1.5 mL) was treated with triethylamine (5 μL, 0.036 mmol), and p-chlorobenzoyl chloride (6 mg, 0.034 mmol) at 0° C. and the resulting mixture was stirred at room temperature for 1 h. The mixture was diluted with methylene chloride (5 mL), washed with saturated sodium bicarbonate, dried (MgSO4) and concentrated. The residue was purified by flash column chromatography on silica gel eluting with ethyl acetate/hexanes to give the title compound (8 mg) as a clear oil: MS (ESI+) 604.2 (M++H).

후처리

  1. washwashed with saturated sodium bicarbonate
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was purified by flash column chromatography on silica gel eluting with ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-0587bf5382f74ec9b474c1c7dcc3d958
출처 데이터셋
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07030118B2

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