Ammonia → 2-[(3R)-3-fluoro-pyrrolidin-1-yl]-6-methyl-4-morpholin-4-yl-benzamide

HRID 515189노트

반응식

HRID 515189 반응식
[F:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:14]=[C:13]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH:12]=[C:11]([CH3:21])[C:8]=2[C:9]#[N:10])[CH2:3]1.N.S(=O)(=O)(O)[OH:24]>>[F:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:14]=[C:13]([N:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)[CH:12]=[C:11]([CH3:21])[C:8]=2[C:9]([NH2:10])=[O:24])[CH2:3]1

참가 물질

4

반응물 3

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 866997552-[(3R)-3-fluoro-pyrrolidin-1-yl]-6-methyl-4-morpholin-4-yl-benzonitrile

생성물 1

HCID 866997572-[(3R)-3-fluoro-pyrrolidin-1-yl]-6-methyl-4-morpholin-4-yl-benzamide수율 68%

실험 절차

A solution of 2-[(3R)-3-fluoro-pyrrolidin-1-yl]-6-methyl-4-morpholin-4-yl-benzonitrile (0.18 g, 0.62 mmol) in sulphuric acid (8 ml) is heated at 100° C. for 1 h. After completion of the reaction (monitored by TLC), the mixture is poured onto ice water. The aqueous layer is basified with aqueous ammonia to pH 10 and extracted with ethyl acetate (3×20 ml). The combined organic layers are washed with water (10 ml), dried over sodium sulfate and concentrated in vacuo yielding 2-[(3R)-3-fluoro-pyrrolidin-1-yl]-6-methyl-4-morpholin-4-yl-benzamide (0.13 g, 0.423 mmol, 68%).

후처리

  1. customAfter completion of the reaction (monitored by TLC)
  2. additionthe mixture is poured onto ice water
  3. extractionextracted with ethyl acetate (3×20 ml)
  4. washThe combined organic layers are washed with water (10 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-2244398160cd4f678c0e7a9ff9942330
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108936B2

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