Hydroxylamine → HCID 11996947, compound

HRID 501223Notes

Reaction equation

HRID 501223 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:17]=[CH:16][C:15]3[NH:14][C:13]4[CH2:18][CH2:19][N:20]([C:22]5[N:27]=[CH:26][C:25]([C:28](OC)=[O:29])=[CH:24][N:23]=5)[CH2:21][C:12]=4[C:11]=3[CH:10]=2)[CH2:4][CH2:3]1.C(Cl)Cl.[NH2:35][OH:36].[OH-].[Na+]>CO.O>[OH:36][NH:35][C:28]([C:25]1[CH:24]=[N:23][C:22]([N:20]2[CH2:19][CH2:18][C:13]3[NH:14][C:15]4[CH:16]=[CH:17][C:9]([CH2:8][N:5]5[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]5)=[CH:10][C:11]=4[C:12]=3[CH2:21]2)=[N:27][CH:26]=1)=[O:29]

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 68461966HCID 68461966, compound

Product 1

HCID 11996947HCID 11996947, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a 0° C. solution of methyl 2-{8-[(4-methylpiperazin-1-yl)methyl]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl}pyrimidine-5-carboxylate (0.1 g) in MeOH:DCM (5:2 mL) was added 50% aqueous hydroxylamine solution (2 mL) and to the mixture was added a solution of NaOH (0.08 g) in water (1 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. After filtering, the solid was dried under vacuum to give N-hydroxy-2-{8-[(4-methylpiperazin-1-yl)methyl]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl}pyrimidine-5-carboxamide (0.075 g). 1H NMR (DMSO-D6, 200 MHz) δ: 10.91 (2H, bm), 8.74 (2H, s), 7.64-7.01 (3H, m), 4.91 (2H, s), 4.19 (2H, s), 3.50-2.88 (10H, m), 2.87 (3H, s); m/e=422.9 (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. filtrationAfter filtering
  6. customthe solid was dried under vacuum

Sources & evidence

ORD record
ord-5b694e0d511d4da1802dc9e71e7f3ed7
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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