Formaldehyde → HCID 46213853, compound

HRID 1182736Notes

Reaction equation

HRID 1182736 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([N:15]4[CH2:20][CH2:19][C:18]5([C:29]6[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=6)[CH2:23][O:22][CH2:21]5)[CH2:17][CH2:16]4)=[N:13][N:14]=[C:10]3[CH2:9][NH:8][CH2:7][C:6]=2[CH:30]=1.C=O.[C:33]([BH3-])#N.[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([N:15]4[CH2:16][CH2:17][C:18]5([C:29]6[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=6)[CH2:23][O:22][CH2:21]5)[CH2:19][CH2:20]4)=[N:13][N:14]=[C:10]3[CH2:9][N:8]([CH3:33])[CH2:7][C:6]=2[CH:30]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67378312HCID 67378312, compound

Product 1

HCID 46213853HCID 46213853, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the crude 1′-(8-chloro-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)-1H-spiro[isochromene-4,4′-piperidine] (0.10 g, 0.24 mmol) and paraformaldehyde (0.057 g, 1.9 mmol) in methanol (2 ml) was heated at reflux for 4 h. After cooling to room temperature sodium cyanoborohydride (0.03 g, 0.47 mmol) was added at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 18 h. Quenching with 1 M aqueous sodium hydroxide solution (30 ml) was followed by extraction with ethyl acetate.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. additionwas added at 0° C
  4. customQuenching with 1 M aqueous sodium hydroxide solution (30 ml)
  5. extractionwas followed by extraction with ethyl acetate

Sources & evidence

ORD record
ord-34038a108af94c6ca96e3f86d1140ccc
Source dataset
uspto-grants-2014_03
Patent number
US08664216B2

Reaction notes

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