Imatinib → HCID 70819096, compound

HRID 2200853Notes

Reaction equation

HRID 2200853 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:21][C:22]([C:24]2[CH:25]=[CH:26][C:27]([CH2:30][N:31]3[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]3)=[CH:28][CH:29]=2)=[O:23])=[CH:6][C:7]=1[NH:8][C:9]1[N:10]=[CH:11][CH:12]=[C:13]([C:15]2[CH:16]=[CH:17][CH:18]=[N:19][CH:20]=2)[N:14]=1.[C:38]([O:44][CH2:45][I:46])(=[O:43])[C:39]([CH3:42])([CH3:41])[CH3:40]>ClCCl>[I-:46].[CH3:37][N+:34]1([CH2:45][O:44][C:38](=[O:43])[C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:33][CH2:32][N:31]([CH2:30][C:27]2[CH:28]=[CH:29][C:24]([C:22](=[O:23])[NH:21][C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[C:7]([NH:8][C:9]4[N:14]=[C:13]([C:15]5[CH:20]=[N:19][CH:18]=[CH:17][CH:16]=5)[CH:12]=[CH:11][N:10]=4)[CH:6]=3)=[CH:25][CH:26]=2)[CH2:36][CH2:35]1

Participants

4

Reactant 2

HCID 5291Imatinib2×HCID 104401Iodomethyl pivalate

Product 1

HCID 70819096HCID 70819096, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Imatinib, N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)-4-((4-methylpiperazin-1-yl)methyl)benzamide, [148] (0.100 g, 0.2 mmol, 1 eq) was dissolved in dichloromethane (10 ml) in a 25 ml two-necked round bottom flask, and iodomethyl pivalate [40] (0.049 g, 0.2 mmol, 1 eq) was added at RT. After stirring for 3-4 hours, the precipitate formed was filtered and washed with DCM to give the product, 1-methyl-4-(4-((4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)carbamoyl)benzyl)-1-((pivaloyloxy)methyl)piperazin-1-ium iodide, [41] as a yellow solid. (0.040 g, 27% yield).

Workup

  1. customthe precipitate formed
  2. filtrationwas filtered
  3. washwashed with DCM

Sources & evidence

ORD record
ord-242804ac0d1f4456a410cdac77ff105e
Source dataset
uspto-grants-2016_06
Patent number
US09359376B2

Reaction notes

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