Methyl iodide → Methanone, [4-[(methylamino)methyl]phenyl](4-methyl-1-piperazinyl)-

HRID 912368Notes

Reaction equation

HRID 912368 reaction equation
C(O[C:6](=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([N:17]2[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]2)=[O:16])=[CH:11][CH:10]=1)(C)(C)C.[H-].[Na+].CI.C(O)(C(F)(F)F)=O>CN(C=O)C>[CH3:6][NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([N:17]2[CH2:18][CH2:19][N:20]([CH3:23])[CH2:21][CH2:22]2)=[O:16])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6422Trifluoroacetic acidHCID 24758Sodium hydrideHCID 67385961HCID 67385961, compound

Product 1

HCID 67385938Methanone, [4-[(methylamino)methyl]phenyl](4-methyl-1-piperazinyl)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A crude product of [4-(4-methyl-piperazine-1-carbonyl)-benzyl]-carbamic acid tert-butyl ester obtained in Example 1-D-293, sodium hydride and methyl iodide were treated in DMF, and further treated with TFA, to obtain (4-methylaminomethyl-phenyl)-(4-methyl-piperazin-1-yl)-methanone. Using bis-(4-methoxy-benzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine (100 mg) and (4-methylaminomethyl-phenyl)-(4-methyl-piperazin-1-yl)-methanone (126 mg) instead of 4-(4-ethyl-piperazin-1-yl)-2,6-difluoro-phenylamine used in Step D in Example 1-D-18, in the same manner as Step D in Example 1-D-18, a crude product of 4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid methyl-[4-(4-methyl-piperazine-1-carbonyl)-benzyl]-amide was obtained, and then the PMB groups were removed according to the above Deprotection method 3, to obtain the desired compound (D-297) as a colorless powder (6 mg, 6%).

Sources & evidence

ORD record
ord-c319f44777554a6895a5e18899840c35
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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