Imatinib → HCID 73669484, compound

HRID 2200854Notes

Reaction equation

HRID 2200854 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]>C(Cl)Cl>[I-:46].[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]([CH2:45][O:44][C:38](=[O:43])[C:39]([CH3:42])([CH3:41])[CH3:40])[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 5291ImatinibHCID 104401Iodomethyl pivalate

Product 1

HCID 73669484HCID 73669484, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Imatinib [148] (0.100 g, 0.2 mmol, 1 eq) was dissolved in DCM (10 ml) in a 25 ml two-necked round bottomed flask and iodomethyl pivalate [40] (0.185 g, 0.77 mmol, 3.8 eq) was added while stirring at RT. After 48 h stirring, the precipitate formed was filtered under vacuum and washed with DCM to give the product, 1-methyl-4-(4-((4-methyl-3-((4-(1-((pivaloyloxy)methyl)pyridin-1-ium-3-yl)pyrimidin-2-yl)amino)phenyl)carbamoyl)benzyl)-1-((pivaloyloxy)methyl)piperazin-1-ium diiodide [42], as a yellow solid. (0.050 g, 25% yield).

Workup

  1. stirringAfter 48 h stirring
  2. customthe precipitate formed
  3. filtrationwas filtered under vacuum
  4. washwashed with DCM

Sources & evidence

ORD record
ord-7cc6dceba64d48deb55f8365358cc48c
Source dataset
uspto-grants-2016_06
Patent number
US09359376B2

Reaction notes

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