Thiomorpholine → HCID 69203497, compound

HRID 2114103Notes

Reaction equation

HRID 2114103 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][N:30]=1)[C:5]([NH:7][C:8]1[CH:9]=[C:10]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([NH:23][CH2:24][CH:25]3[CH2:27][CH2:26]3)=[O:22])=[CH:17][CH:16]=2)[C:11]([CH3:14])=[CH:12][CH:13]=1)=[O:6].[NH:31]1[CH2:36][CH2:35][S:34][CH2:33][CH2:32]1>>[CH:25]1([CH2:24][NH:23][C:21]([C:18]2[CH:19]=[CH:20][C:15]([C:10]3[C:11]([CH3:14])=[CH:12][CH:13]=[C:8]([NH:7][C:5](=[O:6])[C:4]4[CH:28]=[CH:29][N:30]=[C:2]([N:31]5[CH2:36][CH2:35][S:34][CH2:33][CH2:32]5)[CH:3]=4)[CH:9]=3)=[CH:16][CH:17]=2)=[O:22])[CH2:27][CH2:26]1

Participants

3

Reactant 2

HCID 67164ThiomorpholineHCID 44578670HCID 44578670, compound

Product 1

HCID 69203497HCID 69203497, compound

Procedure

A solution of 2-chloro-N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)isonicotinamide (50 mg, 0.12 mmol) in thiomorpholine (1 ml) was heated at 110° C. for 36 h in a sealed tube. The reaction was concentrated under vacuum, the residue triturated with water and purified by preparative HPLC. The solvent was evaporated under vacuum to give N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)-2-thiomorpholin-4-ylisonicotinamide (25 mg). NMR; δH [2H6]—DMSO 10.30,(1H, s), 8.62,(1H, t), 8.25,(1H, d), 7.93,(2H, d), 7.70,(1H, dd), 7.64,(1H, d), 7.44,(2H, d), 7.30,(1H, d), 7.22,(1H, s), 7.03,(1H, d), 3.96,(4H, m), 3.16,(2H, t), 2.62,(4H, m), 2.20,(3H, s), 1.05,(1H, m), 0.43,(2H, m), 0.24,(2H, m). LCMS: retention time 3.57 min, MH+487.

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. customthe residue triturated with water
  3. custompurified by preparative HPLC
  4. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-59f7841d230945ccb7d1e6f3ed013b08
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

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