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Isopropanol → 5,6-difluoro-N-(4-(3-(2-(3-(4-methylpiperazin-1-yl)propylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)-1H-benzo[d]imidazol-2-amine

HRID 252650
Notes
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Reaction equation

HRID 252650 reaction equation
[F:1][C:2]1[C:34]([F:35])=[CH:33][C:5]2[NH:6][C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]4[C:22]([C:23]5[CH:28]=[CH:27][N:26]=[C:25](S(C)(=O)=O)[N:24]=5)=[CH:21][CH:20]=[CH:19][N:18]=4)=[CH:12][CH:11]=3)=[N:8][C:4]=2[CH:3]=1.[CH3:36][N:37]1[CH2:42][CH2:41][N:40]([CH2:43][CH2:44][CH2:45][NH2:46])[CH2:39][CH2:38]1.CC(O)C>C(Cl)Cl>[F:1][C:2]1[C:34]([F:35])=[CH:33][C:5]2[NH:6][C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]4[C:22]([C:23]5[CH:28]=[CH:27][N:26]=[C:25]([NH:46][CH2:45][CH2:44][CH2:43][N:40]6[CH2:39][CH2:38][N:37]([CH3:36])[CH2:42][CH2:41]6)[N:24]=5)=[CH:21][CH:20]=[CH:19][N:18]=4)=[CH:12][CH:11]=3)=[N:8][C:4]=2[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 783281-(3-Aminopropyl)-4-methylpiperazineHCID 668629535,6-difluoro-N-(4-(3-(2-(methylsulfonyl)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)-1H-benzo[d]imidazol-2-amine

Product 1

HCID 589669735,6-difluoro-N-(4-(3-(2-(3-(4-methylpiperazin-1-yl)propylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)-1H-benzo[d]imidazol-2-amine

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
70 °C

Procedure

A resealable pressure vial was charged with 5,6-difluoro-N-(4-(3-(2-(methylsulfonyl)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)-1H-benzo[d]imidazol-2-amine (0.14 g, 0.28 mmol), 3-(4-methylpiperazin-1-yl)propan-1-amine (0.18 g, 1.13 mmol), and 2-propanol (1.89 ml, 0.15 M). The reaction vessel was sealed and the mixture stirred at 70° C. for 16 h. The reaction mixture was cooled to RT, diluted with DCM, and washed with Aq. NaHCO3. The organic layer was collected, dried over Na2SO4, and concentrated to afford brown residue, which was purified by Gilson reverse phase chromatography (10% to 90% CH3CN/H2O/0.1% TFA). The product-containing fractions were combined, basified by addition of aq. NaHCO3 and extracted with ethyl acetate. The organic portion was dried with Na2SO4, filtered, and concentrated to afford pure 5,6-difluoro-N-(4-(3-(2-(3-(4-methylpiperazin-1-yl)propylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)-1H-benzo[d]imidazol-2-amine as a yellow solid. MS m/z=572.2 [M+H]+. Calc'd for C30H31F2N9O: 571.62.

Workup

  1. customThe reaction vessel was sealed
  2. temperatureThe reaction mixture was cooled to RT
  3. washwashed with Aq. NaHCO3
  4. customThe organic layer was collected
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto afford brown residue, which
  8. customwas purified by Gilson reverse phase chromatography (10% to 90% CH3CN/H2O/0.1% TFA)
  9. additionbasified by addition of aq. NaHCO3
  10. extractionextracted with ethyl acetate
  11. dry with materialThe organic portion was dried with Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-5daa4d513aea44d8b97740158da3c6cc
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07868177B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes