Hydroxylamine → HCID 11997256, compound

HRID 501205Notes

Reaction equation

HRID 501205 reaction equation
CO[C:3]([C:5]1[CH:6]=[N:7][C:8]([N:11]2[CH2:36][CH2:35][C:14]3[NH:15][C:16]4[CH:17]=[CH:18][C:19]([C:22]5[O:23][C:24]([CH2:27][N:28]6[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]6)=[CH:25][CH:26]=5)=[CH:20][C:21]=4[C:13]=3[CH2:12]2)=[N:9][CH:10]=1)=[O:4].C(Cl)Cl.[NH2:40][OH:41].[OH-].[Na+]>CO.O>[OH:41][NH:40][C:3]([C:5]1[CH:10]=[N:9][C:8]([N:11]2[CH2:36][CH2:35][C:14]3[NH:15][C:16]4[CH:17]=[CH:18][C:19]([C:22]5[O:23][C:24]([CH2:27][N:28]6[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]6)=[CH:25][CH:26]=5)=[CH:20][C:21]=4[C:13]=3[CH2:12]2)=[N:7][CH:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 68463286HCID 68463286, compound

Product 1

HCID 11997256HCID 11997256, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a 0° C. solution of methyl-2-{8-[5-((4-methylpiperazin-1-yl)methyl)-2-furyl]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl}pyrimidine-5-carboxylate (0.1 g) in methanol:DCM (5:2 mL) was added 50% aqueous hydroxylamine solution (2 mL) and to the mixture was added solution of NaOH (0.8 g) in water (0.5 mL). The reaction mixture was stirred at room temperature for 1 hr and the progress of the reaction was monitored by TLC and upon completion of the reaction the solvent was removed under reduced pressure. The pH of the mixture was adjusted to 7.5 using 1N HCl and the obtained solid was filtered and washed with water followed by diethyl ether and dried under vacuum to give Example 108 (0.08, 64.87%). HPLC: (Rt=11.58); m/e=488 (M+1).

Workup

  1. customthe progress of the reaction was monitored by TLC and upon completion of the reaction the solvent
  2. customwas removed under reduced pressure
  3. filtrationthe obtained solid was filtered
  4. washwashed with water
  5. customdried under vacuum
  6. customto give Example 108 (0.08, 64.87%)

Sources & evidence

ORD record
ord-a617aceb7f6e4d2f8854f4edd957baa0
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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