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

HRID 1474671ノート

反応式

HRID 1474671 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-6b08915cd7e2467e951db02d319fb4a8
出典データセット
uspto-grants-2015_04
特許番号
US09018224B2

反応ノート

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