Ammonium Hydroxide → HCID 87058220, compound

HRID 1972495Notes

Reaction equation

HRID 1972495 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[C@@H:13]([CH2:33][N:34]3[CH2:39][CH2:38][O:37][CH2:36][C@H:35]3[CH3:40])[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[NH4+:42]>CCO>[NH2:42][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[C@@H:13]([CH2:33][N:34]3[CH2:39][CH2:38][O:37][CH2:36][C@@H:35]3[CH3:40])[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 86670366HCID 86670366, compound

Product 1

HCID 87058220HCID 87058220, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

The crude chloropyridine derivative was dissolved in 2 mL of EtOH and 2 mL of 30% aqueous ammonium hydroxide. This solution was heated to 140° C. for 60 min. The mixture was concentrated in vacuo and the crude material was purified via column chromatography (40 g silica gel, 0 to 10% MeOH in CH2Cl2) to give 2-(4-((2S)-4-((6-amino-3-pyridinyl)sulfonyl)-2-(((3S)-3-methyl-4-morpholinyl)methyl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (23 mg) as a foamy solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe crude material was purified via column chromatography (40 g silica gel, 0 to 10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-c738daca9cdc474d8791084078b92e50
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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