Triethylamine → 1-(Cyclopropylmethyl)-3-(4-(1-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperidin-4-yloxy)phenyl)urea

HRID 515265노트

반응식

HRID 515265 반응식
[NH2:1][C:2]1[CH:31]=[CH:30][C:5]([O:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([OH:29])([C:25]([F:28])([F:27])[F:26])[C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[C:32](Cl)(=O)[O:33]C1C=CC([N+]([O-])=O)=CC=1.[CH:45]1([CH2:48][NH2:49])[CH2:47][CH2:46]1.C(N(CC)CC)C>ClCCl.C(=O)(O)[O-].[Na+]>[CH:45]1([CH2:48][NH:49][C:32]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([O:6][CH:7]3[CH2:12][CH2:11][N:10]([CH2:13][C:14]4[CH:15]=[CH:16][C:17]([C:20]([OH:29])([C:21]([F:22])([F:23])[F:24])[C:25]([F:28])([F:26])[F:27])=[CH:18][CH:19]=4)[CH2:9][CH2:8]3)=[CH:30][CH:31]=2)=[O:33])[CH2:47][CH2:46]1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 75646CyclopropanemethanamineHCID 821294-Nitrophenyl chloroformateHCID 86670926HCID 86670926, 화합물

생성물 1

HCID 866709271-(Cyclopropylmethyl)-3-(4-(1-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperidin-4-yloxy)phenyl)urea수율 22.7%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 516892Sodium Bicarbonate용매

실험 절차

A solution of 2-(4-((4-(4-aminophenoxy)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.446 mmol, 200 mg) and 4-nitrophenyl carbonochloridate (0.446 mmol, 90 mg) in dichloromethane (1 mL) were stirred at room temperature for 30 minutes. Cyclopropylmethanamine (0.892 mmol, 0.091 mL, 63.4 mg) was added, followed by triethylamine (1.338 mmol, 0.187 mL, 135 mg) and the reaction stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane and saturated sodium bicarbonate solution was added. The organic layer was separated and concentrated under vacuum. The residue was purified by silica column chromatography (eluent 2-8% methanol in dichloromethane) to give the title compound (55.3 mg). MS (ESI) m/z 546.2 [M+H]+

후처리

  1. additionwas added
  2. customThe organic layer was separated
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by silica column chromatography (eluent 2-8% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-e34084d671af4d3cbfdbc7992cfcd254
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108939B2

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