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

HRID 515272노트

반응식

HRID 515272 반응식
[CH:1]1([CH2:4][NH:5][C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[CH:11][CH:10]=2)=[O:7])[CH2:3][CH2:2]1.[F:22][C:23]([F:40])([F:39])[C:24]([C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=1)([OH:29])[C:25]([F:28])([F:27])[F:26].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl>[CH:1]1([CH2:4][NH:5][C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]3[CH2:21][CH2:20][N:19]([C:34](=[O:35])[C:33]4[CH:32]=[CH:31][C:30]([C:24]([OH:29])([C:23]([F:22])([F:39])[F:40])[C:25]([F:26])([F:27])[F:28])=[CH:38][CH:37]=4)[CH2:18][CH2:17]3)=[CH:11][CH:10]=2)=[O:7])[CH2:2][CH2:3]1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 5911694-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)benzoic acidHCID 671941431-(Cyclopropylmethyl)-3-(4-(piperidin-4-yloxy)phenyl)urea

생성물 1

HCID 866709311-(Cyclopropylmethyl)-3-(4-(1-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzoyl)piperidin-4-yloxy)phenyl)urea수율 4.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

1-(cyclopropylmethyl)-3-(4-(piperidin-4-yloxy)phenyl)urea (1.037 mmol, 300 mg), 4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzoic acid (1.037 mmol, 299 mg) and triethylamine (3.11 mmol, 0.432 mL, 315 mg) were combined and stirred at room temperature in dichloromethane (5 mL). 1-Propanephosphonic acid cyclic anhydride (1.555 mmol, 0.926 mL, 990 mg; 50% solution in ethyl acetate) was added and the reaction stirred at room temperature for 1 hour. The reaction mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried and concentrated under vacuum. The residue was dissolved in dichloromethane and purified by silica column chromatography (eluent 2-8% methanol in dichloromethane) to afford the title compound (24 mg). MS (ESI) m/z 560.2 [M+H]+

후처리

  1. washThe reaction mixture was washed with saturated sodium bicarbonate solution
  2. customthe organic layer was separated
  3. customdried
  4. concentrationconcentrated under vacuum
  5. dissolutionThe residue was dissolved in dichloromethane
  6. custompurified by silica column chromatography (eluent 2-8% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-0ded12cd041946dab3aa486ce8856361
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108939B2

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