Formaldehyde → HCID 73214394, compound

HRID 2200897Notes

Reaction equation

HRID 2200897 reaction equation
C=O.[C:3](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:17]1[C:20]2([CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH2:19][CH:18]1[CH2:26][NH:27][C:28]([C:30]1[C:31]([NH:42][CH2:43][C:44]2[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[C:46]([Cl:52])[CH:45]=2)=[N:32][C:33]([N:36]2[CH2:41][CH:40]3[CH:38]([CH2:39]3)[CH2:37]2)=[N:34][CH:35]=1)=[O:29]>C1COCC1>[CH:38]12[CH2:39][CH:40]1[CH2:41][N:36]([C:33]1[N:32]=[C:31]([NH:42][CH2:43][C:44]3[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[C:46]([Cl:52])[CH:45]=3)[C:30]([C:28]([NH:27][CH2:26][CH:18]3[CH2:19][C:20]4([CH2:21][CH2:22][N:23]([CH3:3])[CH2:24][CH2:25]4)[CH2:17]3)=[O:29])=[CH:35][N:34]=1)[CH2:37]2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 118158105HCID 118158105, compound

Product 1

HCID 73214394HCID 73214394, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF (20 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. Formalin (1 mL) was added. The reaction was conducted at ambient temperature for 1 h, sodium triacetoxyborohydride (134 mg, 0.63 mmol) was added and the reaction was continued for 4 h. The reaction was quenched with water. The reaction mixture was filtrated. 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-formamide (39 mg, 21% yield).

Workup

  1. waitthe reaction was continued for 4 h
  2. customThe reaction was quenched with water
  3. filtrationThe reaction mixture was filtrated
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. customThe obtained solid was purified by silica gel column chromatography (DCM/methanol=20/1)

Sources & evidence

ORD record
ord-67f8c9a71fff4c7c9449ccaf767b92f8
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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