Morpholine → HCID 69271847, compound

HRID 2040103Notes

Reaction equation

HRID 2040103 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[C:20]([CH:22]=[C:23]2[S:27][C:26](SC)=[N:25][C:24]2=[O:30])[CH:19]=[CH:18][C:4]=1[O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=1[C:14]([F:17])([F:16])[F:15].[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1.[Al]>CC#N>[CH3:1][O:2][C:3]1[CH:21]=[C:20]([CH:22]=[C:23]2[S:27][C:26]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[N:25][C:24]2=[O:30])[CH:19]=[CH:18][C:4]=1[O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=1[C:14]([F:16])([F:17])[F:15]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 5359268AluminumHCID 69041534HCID 69041534, compound

Product 1

HCID 69271847HCID 69271847, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-[2-Methoxy-4-(2-methylsulfanyl-4-oxo-4H-thiazol-5-ylidenemethyl)-phenoxy]-3-trifluoromethyl-benzonitrile (88 mg, 0.2 mmol) in CH3CN (1 mL) was treated with morpholine (0.4 mmol) and heated to 60° C. in an aluminum heating block for 10 h. The solvent was removed in vacuo and the crude reaction mixture was purified by silica gel chromatography (EtOAc/CH2Cl2) to afford the title compound. 1H NMR (400 Hz, CDCl3) δ 7.95 (d, 1H), 7.79 (s, 1H), 7.66 (dd, 1H), 7.19 (m, 3H), 6.76 (d, 1H), 4.10 (m, 2H), 3.84 (m, 4H), 3.78 (s, 3H), 3.64 (m, 2H); LC/MS (m/z) [M+1]+490.3 (calculated for C23H19F3N3O4S, 490.47).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude reaction mixture
  3. customwas purified by silica gel chromatography (EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-21393ff6ec874f159cdca0a9696953bb
Source dataset
uspto-grants-2013_11
Patent number
US08580832B2

Reaction notes

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