1H-1,2,4-Triazole → 6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-3-(1H-1,2,4-triazol-1-yl)-1,2-benzoxazole-5-carbaldehyde

HRID 245536노트

반응식

HRID 245536 반응식
Cl[C:2]1[C:6]2[CH:7]=[C:8]([CH:20]=[O:21])[C:9]([N:12]3[CH2:17][C@H:16]([CH3:18])[O:15][C@H:14]([CH3:19])[CH2:13]3)=[C:10]([F:11])[C:5]=2[O:4][N:3]=1.C1CCN2C(=NCCC2)CC1.[NH:33]1[CH:37]=[N:36][CH:35]=[N:34]1>C(#N)C>[CH3:19][C@H:14]1[O:15][C@@H:16]([CH3:18])[CH2:17][N:12]([C:9]2[C:8]([CH:20]=[O:21])=[CH:7][C:6]3[C:2]([N:33]4[CH:37]=[N:36][CH:35]=[N:34]4)=[N:3][O:4][C:5]=3[C:10]=2[F:11])[CH2:13]1

참가 물질

5

반응물 3

HCID 92571H-1,2,4-TriazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 866581213-chloro-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-1,2-benzoxazole-5-carbaldehyde2회

생성물 1

HCID 866581276-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-3-(1H-1,2,4-triazol-1-yl)-1,2-benzoxazole-5-carbaldehyde

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
100 °C

실험 절차

To a solution of 3-chloro-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-1,2-benzoxazole-5-carbaldehyde (Intermediate 534, 0.2 g, 0.68 mmol) in acetonitrile was added DBU (0.19 mL, 1.28 mmol) followed by 1,2,4-triazole (0.053 g, 0.76 mmol), and the mixture was stirred at 100° C. for 12 hours. The reaction mixture was concentrated, the residue was purified by silica gel column chromatography using EtOAc in pet. ether to give title product.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-1af048b5836c4053b13169d9e4274596
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658641B2

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