Methanol → HCID 178465575, compound

HRID 499721Notes

Reaction equation

HRID 499721 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:26])=[C:6]([NH:8][C:9]2[S:10][C:11](=[CH:15][C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[N:22]=[CH:21][CH:20]=[CH:19]4)[C:12](=[O:14])[N:13]=2)[CH:7]=1.Cl.[C:28](=[NH:31])(S)[CH3:29].CO>CN(C=O)C>[ClH:26].[Cl:26][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:28](=[NH:31])[CH3:29])=[CH:7][C:6]=1[NH:8][C:9]1[S:10][C:11](=[CH:15][C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[N:22]=[CH:21][CH:20]=[CH:19]3)[C:12](=[O:14])[N:13]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 178465710HCID 178465710, compoundHCID 178507594HCID 178507594, compound

Product 1

HCID 178465575HCID 178465575, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred, cooled (0 deg.) solution of 2-(5-amino-2-chloro-phenylamino)-5-quinolin-6-ylmethylene-thiazol-4-one (39.7 mg, 0.1 mmol) in DMF (1 ml) was added thioacetimidate hydrochloride 9 (28 mg, 0.11 mmol). The mixture was warmed to room temperature and stirred for over night. DMF was removed by nitrogen gas blowing and resulting oil was dissolved with methanol. Insoluble solid was collected by filtration and washed with methanol, followed by desiccation in vacuo to afford the title (14 mg, 0.031 mmol).

Workup

  1. customDMF was removed by nitrogen gas
  2. customresulting oil
  3. filtrationInsoluble solid was collected by filtration
  4. washwashed with methanol
  5. customto afford the title (14 mg, 0.031 mmol)

Sources & evidence

ORD record
ord-b7256afb6f894e019c1a43c08f7ded7d
Source dataset
uspto-grants-2010_08
Patent number
US07767701B2

Reaction notes

Loading…