Triethylamine → HCID 86638572, 화합물

HRID 1807783노트

반응식

HRID 1807783 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[F:11].[F:12][C:13]([F:35])([F:34])[C:14]([C:20]1[CH:33]=[CH:32][C:23]([CH2:24][N:25]2[CH2:30][CH2:29][NH:28][CH2:27][C:26]2=[O:31])=[CH:22][CH:21]=1)([OH:19])[C:15]([F:18])([F:17])[F:16].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:28]2[CH2:29][CH2:30][N:25]([CH2:24][C:23]3[CH:32]=[CH:33][C:20]([C:14]([OH:19])([C:13]([F:12])([F:34])[F:35])[C:15]([F:18])([F:16])[F:17])=[CH:21][CH:22]=3)[C:26](=[O:31])[CH2:27]2)=[O:8])=[CH:4][C:3]=1[F:11]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 99714-Amino-3-fluorobenzoic acidHCID 111923Propylphosphonic anhydrideHCID 86638571HCID 86638571, 화합물

생성물 1

HCID 86638572HCID 86638572, 화합물수율 56.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirring solution of 4-amino-3-fluorobenzoic acid (1.965 mmol, 305 mg), 1-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-2-one (1.965 mmol, 700 mg) and triethylamine (5.89 mmol, 596 mg) in dichloromethane (10 mL) was added 1-propanephosphonic acid cyclic anhydride (2.95 mmol, 1876 mg; 50% solution in ethyl acetate). The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with dichloromethane (20 mL) and washed with saturated aqueous sodium hydrogen carbonate solution (30 mL). The organic phase was concentrated and the resulting residue was purified by column chromatography on silica gel (eluting with 50% ethyl acetate/50% dichloromethane—100% ethyl acetate gradient) to afford the title compound (550 mg). MS (ESI) m/z 492.3 [M−H]−

후처리

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution (30 mL)
  2. concentrationThe organic phase was concentrated
  3. customthe resulting residue was purified by column chromatography on silica gel (eluting with 50% ethyl acetate/50% dichloromethane—100% ethyl acetate gradient)

출처 및 근거

ORD 기록
ord-24381c991c9b4fd18719b1c5e1e80714
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08357679B2

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