Ammonia → HCID 17882366, compound

HRID 365624Notes

Reaction equation

HRID 365624 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:23][S:24]([CH2:27][CH2:28][O:29]C(=O)C)(=[O:26])=[O:25])[CH:5]=[CH:6][C:7]=1[CH2:8][C:9]1[N:10]([CH3:22])[C:11]([C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:12][CH:13]=1.N>CO>[F:1][C:2]1[CH:3]=[C:4]([NH:23][S:24]([CH2:27][CH2:28][OH:29])(=[O:25])=[O:26])[CH:5]=[CH:6][C:7]=1[CH2:8][C:9]1[N:10]([CH3:22])[C:11]([C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 17882414HCID 17882414, compound

Product 1

HCID 17882366HCID 17882366, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

N-{3-Fluoro-4-[5-benzoyl-1-methyl-1H-pyrrol-2-ylmethyl]phenyl}-2-(acetoxy)-ethanesulfonamide (0.415 g, 0.905 mmol) [prepared as in Example 18, Step (a)] was dissolved in methanol (5 ml) and a 2.0 M solution of ammonia in methanol (4.53 ml, 9.05 mmol) was added. The mixture was stirred for 60 h, after which it was concentrated to dryness. Purification of the residue by flash chromatography gave N-{3-fluoro-4-[5-benzoyl-1-methyl-1H-pyrrol-2-ylmethyl]phenyl}-2-(hydroxy)-ethanesulfonamide (282 mg, 75%) as a solid.

Workup

  1. concentrationafter which it was concentrated to dryness
  2. customPurification of the residue by flash chromatography

Sources & evidence

ORD record
ord-a8bc5e052b7140218090901ae91e7d79
Source dataset
uspto-grants-2000_10
Patent number
US06127402

Reaction notes

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