Ammonia → HCID 54277563, compound

HRID 394607Notes

Reaction equation

HRID 394607 reaction equation
N.C1(S([N:11]2[C:19]3[CH:18]=[CH:17][N:16]=[C:15]([Cl:20])[C:14]=3[CH:13]=[C:12]2[CH2:21][N:22]2[CH2:26][CH2:25][C@H:24]([NH:27][S:28]([C:31]3[S:35][C:34]4[CH:36]=[C:37]([Cl:40])[CH:38]=[CH:39][C:33]=4[CH:32]=3)(=[O:30])=[O:29])[C:23]2=[O:41])(=O)=O)C=CC=CC=1>CO>[Cl:20][C:15]1[C:14]2[CH:13]=[C:12]([CH2:21][N:22]3[CH2:26][CH2:25][C@H:24]([NH:27][S:28]([C:31]4[S:35][C:34]5[CH:36]=[C:37]([Cl:40])[CH:38]=[CH:39][C:33]=5[CH:32]=4)(=[O:29])=[O:30])[C:23]3=[O:41])[NH:11][C:19]=2[CH:18]=[CH:17][N:16]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86757281HCID 86757281, compound

Product 1

HCID 54277563HCID 54277563, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ammonia gas is bubbled for 5 minutes into a solution of 6-chloro-benzo[b]thiophene-2-sulfonic acid[1-(1-benzenesulfonyl-4-chloro-1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-amide (0.14 g, 0.22 mmol) in MeOH (10 mL). The solution is refluxed overnight then concentrated to dryness. The crude product is purified by column chromatography eluting with 5% MeOH/CH2Cl2 to give the product (0.065 g, 0.13 mmol) as a white solid.

Workup

  1. temperatureThe solution is refluxed overnight
  2. concentrationthen concentrated to dryness
  3. customThe crude product is purified by column chromatography
  4. washeluting with 5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-07acde47dadd4de7bbcf1237435890e0
Source dataset
uspto-grants-2003_08
Patent number
US06602864B1

Reaction notes

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