Formaldehyde → HCID 73214470, compound

HRID 2200900Notes

Reaction equation

HRID 2200900 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH2:5][NH:6][C:7]1[C:12]([C:13]([NH:15][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[O:14])=[CH:11][N:10]=[C:9]([N:24]2[CH2:30][CH2:29][C:26]3([CH2:28][CH2:27]3)[CH2:25]2)[N:8]=1.[CH2:36]=O.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH2:5][NH:6][C:7]1[C:12]([C:13]([NH:15][CH2:16][CH2:17][N:18]2[CH2:19][CH2:20][N:21]([CH3:36])[CH2:22][CH2:23]2)=[O:14])=[CH:11][N:10]=[C:9]([N:24]2[CH2:30][CH2:29][C:26]3([CH2:27][CH2:28]3)[CH2:25]2)[N:8]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 73214396HCID 73214396, compound

Product 1

HCID 73214470HCID 73214470, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (20 mL) was dissolved 4-((3-chloro-4-methoxybenzyl)amino)-N-(2-(piperazin-1-yl)ethyl)-2-(5-azaspiro[2.4]heptan-5-yl)pyrimidine-5-formamide (250 mg, 0.5 mmol). Formalin (37%, 61 mg, 0.75 mmol) was added. The reaction was conducted at 0° C. for 1 h. Sodium borohydride (38 mg, 1.0 mmol) was added at 0° C. The reaction was continued for 2 h, then quenched with water. The reaction mixture was filtrated, dried and concentrated to give 4-((3-chloro-4-methoxybenzyl)amino)-N-(2-(4-methylpiperazin-1-yl)ethyl)-2-(5-azaspiro[2.4]heptan-5-yl)pyrimidine-5-formamide (168 mg, 65% yield). The product was dissolved in methanol (5 mL), and hydrochloric acid (0.1 mL) was added. The reaction mixture was stirred at ambient temperature for 30 min. The solvent was removed by evaporation to give the hydrochloride salt of the compound as a white solid.

Workup

  1. waitThe reaction was continued for 2 h
  2. customquenched with water
  3. filtrationThe reaction mixture was filtrated
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bf12a3cff84f4c38867cdcfbc54a0e4f
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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