Methylamine → TAS-115

HRID 1873689Notes

Reaction equation

HRID 1873689 reaction equation
Cl.[F:2][C:3]1[CH:24]=[C:23]([NH:25][C:26]([NH:28][C:29](=[O:37])[CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[S:27])[CH:22]=[CH:21][C:4]=1[O:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:19][CH3:20])=[C:13]([C:16]([OH:18])=O)[CH:14]=2)[N:9]=[CH:8][CH:7]=1.[CH3:38][NH2:39]>O1CCCC1>[F:2][C:3]1[CH:24]=[C:23]([NH:25][C:26]([NH:28][C:29](=[O:37])[CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[S:27])[CH:22]=[CH:21][C:4]=1[O:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:19][CH3:20])=[C:13]([C:16]([NH:39][CH3:38])=[O:18])[CH:14]=2)[N:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 866506984-(2-Fluoro-4-(3-(2-phenylacetyl)thioureido)phenoxy)-7-methoxyquinoline-6-carboxylic acid hydrochloride

Product 1

HCID 44247727TAS-115Yield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

Similar to the synthesis of Example 1, compound 1e (20 mg), 40% aqueous solution of methylamine (5 μL), and DMTMM•n-hydrate (22 mg) were dissolved in tetrahydrofuran (1 mL), followed by stirring at 30° C. for 1 hour, to thereby yield the titled compound 6 (18.4 mg, yield: 96%).

Sources & evidence

ORD record
ord-809a1e33691c49f887541474d6bdfa5e
Source dataset
uspto-grants-2012_11
Patent number
US08304427B2

Reaction notes

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