Sodium hydride → HCID 70695469, compound

HRID 1958045Notes

Reaction equation

HRID 1958045 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:5]([CH3:26])=[C:6]([CH2:10][NH:11][C:12]2[N:13]=[C:14]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[S:15][C:16]=2[C:17]([NH2:19])=[O:18])[CH:7]=[CH:8][CH:9]=1.[C:27](N1C=CN=C1)(N1C=CN=C1)=[S:28]>O1CCCC1>[Cl:3][C:4]1[C:5]([CH3:26])=[C:6]([CH2:10][N:11]2[C:12]3[N:13]=[C:14]([N:20]4[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)[S:15][C:16]=3[C:17](=[O:18])[NH:19][C:27]2=[S:28])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 802641,1'-ThiocarbonyldiimidazoleHCID 66779830HCID 66779830, compound

Product 1

HCID 70695469HCID 70695469, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (0.447 g, 17.71 mmol) was added portionwise to a suspension of 4-{[(3-chloro-2-methylphenyl)methyl]amino}-2-(4-morpholinyl)-1,3-thiazole-5-carboxamide (0.812 g, 2.213 mmol) and 1,1′-thiocarbonyldiimidazole (1.183 g, 6.64 mmol) in Tetrahydrofuran (THF) (20 mL). The mixture was stirred at rt for 2.5 days, then quenched by the dropwise addition of saturated NH4Cl solution. The solvent was evaporated in vacuo and the residue was suspended in water. The pH was adjusted to about 6 by the addition of 1 N HCl. The yellowish orange solid was collected by filtration, washed with water, and dried in a vacuum oven at 65 C to provide 887 mg of the titled compound (98% yield). LC/MS: MS (ES+) m/e 409 (MH+)

Workup

  1. customquenched by the dropwise addition of saturated NH4Cl solution
  2. customThe solvent was evaporated in vacuo
  3. additionThe pH was adjusted to about 6 by the addition of 1 N HCl
  4. filtrationThe yellowish orange solid was collected by filtration
  5. washwashed with water
  6. customdried in a vacuum oven at 65 C

Sources & evidence

ORD record
ord-b998501f93ce475d9d0303aed3cfc69b
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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