Dimethylamine → 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide

HRID 41165

반응식

HRID 41165 반응식
C[CH2:2][N:3](C(C)C)[CH:4](C)C.[F:10][C:11]1[CH:12]=[C:13]([N:18]2[CH2:22][CH2:21][CH2:20][CH:19]2[C:23]2[CH:24]=[C:25]([C:40](O)=[O:41])[CH:26]=[C:27]3[C:32]=2[O:31][C:30]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)=[CH:29][C:28]3=[O:39])[CH:14]=[C:15]([F:17])[CH:16]=1.[B-](F)(F)(F)F.CN(C(ON1C(=O)CCC1=O)=[N+](C)C)C.CNC>CN(C=O)C>[F:17][C:15]1[CH:14]=[C:13]([N:18]2[CH2:22][CH2:21][CH2:20][CH:19]2[C:23]2[CH:24]=[C:25]([C:40]([N:3]([CH3:4])[CH3:2])=[O:41])[CH:26]=[C:27]3[C:32]=2[O:31][C:30]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)=[CH:29][C:28]3=[O:39])[CH:12]=[C:11]([F:10])[CH:16]=1

참가 물질

6

반응물 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 866724028-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid

생성물 1

HCID 665592438-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide수율 68.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

DIPEA (0.046 mL, 0.26 mmol) was added to a suspension of 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (60 mg, 0.13 mmol) in DMF (1 mL) followed by TSTU (43.5 mg, 0.14 mmol) at room temperature under nitrogen and stirred overnight. Dimethylamine (2N in THF) (0.131 mL, 0.26 mmol) was then added and the mixture was stirred for another hour. The reaction mixture was purified by preparative HPLC. The fractions were evaporated to dryness, the residue was taken up in a minimum of DCM, diluted with petroleum ether, stirred for 3 h, collected by filtration and dried to afford 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (43 mg, 68%) as a white solid.

후처리

  1. stirringthe mixture was stirred for another hour
  2. customThe reaction mixture was purified by preparative HPLC
  3. customThe fractions were evaporated to dryness
  4. additiondiluted with petroleum ether
  5. stirringstirred for 3 h
  6. filtrationcollected by filtration
  7. customdried

출처 및 근거

ORD 기록
ord-88b8afdafbdc459ba5898bdf1e8dce85
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530470B2

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