Ammonia → HCID 17882366, compound

HRID 369405Notes

Reaction equation

HRID 369405 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-1d9d7c96091f471882e920687dc7fd09
Source dataset
uspto-grants-2000_10
Patent number
US06136844

Reaction notes

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