Formaldehyde → HCID 2209782, compound

HRID 339545Notes

Reaction equation

HRID 339545 reaction equation
[C:1]([BH3-])#[N:2].[Na+].N[C:6]1[CH:30]=[CH:29][C:9]([C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[S:20][C:21]4[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:22]=4[N:23]=3)=[CH:15][CH:14]=2)=[O:11])=[CH:8][CH:7]=1.C=O.[CH3:33]CCCCC.CCOC(C)=O>CC(O)=O>[CH3:33][N:2]([CH3:1])[C:6]1[CH:30]=[CH:29][C:9]([C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[S:20][C:21]4[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:22]=4[N:23]=3)=[CH:15][CH:14]=2)=[O:11])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21226206Ethyl acetate hexaneHCID 58341983HCID 58341983, compound

Product 1

HCID 2209782HCID 2209782, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Prepared as described in the Amination section using sodium cyanoborohydride (0.44 g, 6.95 mmol), 4-amino-N-[4-(6-methylbenzothiazol-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 (0.04 g, 7%) as a colourless solid after work-up and flash chromatography (3:1 Hexane/EtOAc).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-97d1d9777af14de49dc98f133f7c9d5d
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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