Sodium hydride → HCID 18670449, compound

HRID 1059396Notes

Reaction equation

HRID 1059396 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[S:11][C:10]3[N:12]=[CH:13][CH:14]=[N:15][C:9]=3[N:8]([CH2:16][O:17][CH3:18])[C:7]=2[CH:19]=1.[CH3:20][C:21]1[CH:30]=[C:29]([NH2:31])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1.[H-].[Na+]>>[CH3:20][C:21]1[CH:30]=[C:29]([NH:31][CH2:2][C:3]2[CH:4]=[CH:5][C:6]3[S:11][C:10]4[N:12]=[CH:13][CH:14]=[N:15][C:9]=4[N:8]([CH2:16][O:17][CH3:18])[C:7]=3[CH:19]=2)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 811164-Amino-2-methylquinolineHCID 1133536310-methoxymethyl-8-chloromethyl-10H-pyrazino[2,3-b][1,4]benzothiazine

Product 1

HCID 18670449HCID 18670449, compoundYield 95.1%

Procedure

Similar to Example 1094, 307 mg of 8-chloromethyl-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine was treated with 354 mg of 2-methyl-4-aminoquinoline in the presence of 91 mg of sodium hydride (60% oily) to thereby give 413 mg of 8-[(2-methylquinolin-4-yl)aminomethyl]-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine as a yellow oily substance. Then this product was deblocked by the same method as the one of Example 9 to thereby give 114 mg of the title compound as, yellow crystals.

Sources & evidence

ORD record
ord-b69d50c30a6b49f1bc14925d71774a69
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

Loading…