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

HRID 515189Notes

Reaction equation

HRID 515189 reaction equation
[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

Participants

4

Reactant 3

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 86699755HCID 86699755, compound

Product 1

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

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-2244398160cd4f678c0e7a9ff9942330
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

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