Formaldehyde → HCID 5194646, compound

HRID 339544Notes

Reaction equation

HRID 339544 reaction equation
[C:1]([BH3-])#[N:2].[Na+].N[C:6]1[CH:7]=[C:8]([CH:28]=[CH:29][CH:30]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[S:19][C:20]3[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:21]=3[N:22]=2)=[CH:14][CH:13]=1)=[O:10].C=O.[CH3:33]CCCCC.CCOC(C)=O>CC(O)=O>[CH3:33][N:2]([CH3:1])[C:6]1[CH:7]=[C:8]([CH:28]=[CH:29][CH:30]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[S:19][C:20]3[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:21]=3[N:22]=2)=[CH:14][CH:13]=1)=[O:10]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 10361109HCID 10361109, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 5194646HCID 5194646, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Prepared as described in the Amination section using sodium cyanoborohydride (0.44 g, 6.95 mmol), 3-amino-N-[4-(6-methyl benzothiazol-2-yl)-phenyl]-benzamide (0.50 g, 1.39 mmol) and paraformaldehyde (0.42 g, 13.9 mmol) in AcOH (8 ml) to give the title compound (0.15 g, 28%) as a colourless solid after work-up and flash chromatography (2:1 Hexane/EtOAc).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-45767f4dd2404fd3b5f5fb8331c7a6d7
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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