Formaldehyde → HCID 67312782, compound

HRID 339525Notes

Reaction equation

HRID 339525 reaction equation
[C:1]([BH3-])#[N:2].[Na+].N[C:6]1[CH:31]=[CH:30][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]([O:28][CH3:29])[CH:25]=[CH:24][C:22]=4[N:23]=3)=[CH:15][CH:14]=2)=[O:11])=[C:8]([C:32]([F:35])([F:34])[F:33])[CH:7]=1.C=O.[CH2:38](Cl)Cl.CCOC(C)=O>CC(O)=O>[CH3:38][N:2]([CH3:1])[C:6]1[CH:31]=[CH:30][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]([O:28][CH3:29])[CH:25]=[CH:24][C:22]=4[N:23]=3)=[CH:15][CH:14]=2)=[O:11])=[C:8]([C:32]([F:35])([F:34])[F:33])[CH:7]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21226138Dichloromethane ethylacetateHCID 67313401HCID 67313401, compound

Product 1

HCID 67312782HCID 67312782, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Prepared as described in the Amination section using sodium cyanoborohydride (66 mg, 1.05 mmol), 4-amino-2-trifluoromethyl-N-[4-(6-methoxybenzothiazol-2-yl)-phenyl]-benzamide (100 mg, 0.226 mmol) and paraformaldehyde (63 mg, 2.11 mmol) in AcOH (3 ml) to give the title compound (39 mg, 37%) as a colourless solid after work-up and flash chromatography (20:1 DCM/EtOAc).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-0ec6fd05c4af47f68f86dc258203939a
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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