5-(2-methylsulfonyl-pyrimidin-4-yl)-thiophene-2sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide → HCID 10695653, compound

HRID 1636785Notes

Reaction equation

HRID 1636785 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:31]=[CH:32][CH:33]=1)[CH2:6][N:7]1[CH2:11][CH2:10][C@H:9]([NH:12][S:13]([C:16]2[S:17][C:18]([C:21]3[CH:26]=[CH:25][N:24]=[C:23](S(C)=O)[N:22]=3)=[CH:19][CH:20]=2)(=[O:15])=[O:14])[C:8]1=[O:30])#[N:2].C(C1C=C(C=CC=1)CN1CC[C@H](NS(C2SC(C3C=CN=C(S(C)(=O)=O)N=3)=CC=2)(=O)=O)[C:41]1=[O:64])#N>CO>[C:1]([C:3]1[CH:4]=[C:5]([CH:31]=[CH:32][CH:33]=1)[CH2:6][N:7]1[CH2:11][CH2:10][C@H:9]([NH:12][S:13]([C:16]2[S:17][C:18]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([O:64][CH3:41])[N:22]=3)=[CH:19][CH:20]=2)(=[O:15])=[O:14])[C:8]1=[O:30])#[N:2]

Participants

4

Reactant 2

HCID 105060725-(2-methylsulfonyl-pyrimidin-4-yl)-thiophene-2sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amideHCID 106252395-(2-methylsulfinyl-pyrimidin-4-yl)-thiophene-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin3-(S)-yl]-amide

Product 1

HCID 10695653HCID 10695653, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of [5-(2-methylsulfinyl-pyrimidin-4-yl)-thiophene-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide and [5-(2-methylsulfonyl-pyrimidin-4-yl)-thiophene-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide (0.19 g, 0.37 mmol) is dissolved in 10 mL of MeOH and 1 mL of CH2Cl2 and NH3 gas is bubbled through the solution for 5 minutes. The resulting mixture is heated at reflux for 4 hours. After this time, the solution is concentrated in vacuo to give the title compound (0.17 g, 0.36 mmol) as a solid.

Workup

  1. custom1 mL of CH2Cl2 and NH3 gas is bubbled through the solution for 5 minutes
  2. temperatureThe resulting mixture is heated
  3. temperatureat reflux for 4 hours
  4. concentrationAfter this time, the solution is concentrated in vacuo

Sources & evidence

ORD record
ord-5d73a1e59fc346e68622907738e02b03
Source dataset
uspto-grants-2000_03
Patent number
US06034093

Reaction notes

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