Formaldehyde → HCID 73214394, compound

HRID 2200898Notes

Reaction equation

HRID 2200898 reaction equation
[CH2:1]1[C:4]2([CH2:9][CH2:8][NH:7][CH2:6][CH2:5]2)[CH2:3][CH:2]1[CH2:10][NH:11][C:12]([C:14]1[C:15]([NH:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([Cl:36])[CH:29]=2)=[N:16][C:17]([N:20]2[CH2:25][CH:24]3[CH:22]([CH2:23]3)[CH2:21]2)=[N:18][CH:19]=1)=[O:13].[CH2:37]=O.[BH4-].[Na+]>CO>[CH:22]12[CH2:23][CH:24]1[CH2:25][N:20]([C:17]1[N:16]=[C:15]([NH:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([Cl:36])[CH:29]=3)[C:14]([C:12]([NH:11][CH2:10][CH:2]3[CH2:3][C:4]4([CH2:5][CH2:6][N:7]([CH3:37])[CH2:8][CH2:9]4)[CH2:1]3)=[O:13])=[CH:19][N:18]=1)[CH2:21]2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 118158105HCID 118158105, compound

Product 1

HCID 73214394HCID 73214394, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (50 mL) was dissolved the above N-(7-azaspiro[3.5]nonan-2-ylmethyl)-2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)pyrimidine-5-formamide (357 mg, 0.7 mmol). Formalin (284 mg, 3.5 mmol) was added. Sodium borohydride (133 mg, 3.5 mmol) was added slowly. The reaction was continued for 10 h then quenched with water. The reaction mixture was extracted with ethyl acetate. The organic phase was dried and concentrated. The obtained solid was purified by silica gel column chromatography (DCM/methanol=20/1) to give 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)-N-((7-methyl-7-azaspiro[3.5]nonan-2-yl)methyl)pyrimidine-5-form amide (100 mg, 27.4% yield).

Workup

  1. customthen quenched with water
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customThe obtained solid was purified by silica gel column chromatography (DCM/methanol=20/1)

Sources & evidence

ORD record
ord-995df5322fc749bd9b50c4201133fd6a
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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