Ammonia → HCID 17882366, compound

HRID 618340Notes

Reaction equation

HRID 618340 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-8c877158cdc34ff69e1dd02bfa7ff81f
Source dataset
uspto-grants-1999_09
Patent number
US05952368

Reaction notes

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