Triphenylphosphine → 2-[4-(2-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethoxy)-2-methylphenyl]-N,N-dimethylacetamide

HRID 1474671노트

반응식

HRID 1474671 반응식
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C@H:14]3[CH2:16][C@H:15]3[CH2:17][CH2:18][OH:19])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.O[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([N:30]([CH3:32])[CH3:31])=[O:29])=[C:23]([CH3:33])[CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C@H:14]3[CH2:16][C@H:15]3[CH2:17][CH2:18][O:19][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][C:28]([N:30]([CH3:31])[CH3:32])=[O:29])=[C:23]([CH3:33])[CH:22]=3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 581286112-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethanolHCID 867111812-(4-hydroxy-2-methylphenyl)-N,N-dimethylacetamide

생성물 1

HCID 715731762-[4-(2-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethoxy)-2-methylphenyl]-N,N-dimethylacetamide

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

2-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethanol (90 mg, 0.319 mmol) was dissolved in toluene (1 ml) and 2-(4-hydroxy-2-methylphenyl)-N,N-dimethylacetamide (62 mg, 0.319 mmol), triphenylphosphine (126 mg, 0.479 mmol), and DIAD (93 μl, 0.479 mmol) added and the mixture stirred at RT overnight. The mixture was concentrated in vacuo and the residue purified by chromatography using a Biotage RP C18 cartridge (30 g) using a gradient eluant of 10-100% water:acetonitrile+0.1% TFA to afford the title compound. LC/MS (m/z): 457 (M+H)+. GPR119 Human EC50: 1.7 nM.

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue purified by chromatography

출처 및 근거

ORD 기록
ord-6b08915cd7e2467e951db02d319fb4a8
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018224B2

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