Formamide → 5-[4-(Benzyloxy)phenyl]-1-(4-methoxyphenyl)-N,N-dimethyl-1H-pyrazol-3-amine

HRID 351199Notes

Reaction equation

HRID 351199 reaction equation
[CH:1]([NH2:3])=O.[C:4]([BH3-])#N.[Na+].[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:26]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[N:25]=[C:24](N)[CH:23]=2)=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CO>[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:26]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[N:25]=[C:24]([N:3]([CH3:1])[CH3:4])[CH:23]=2)=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 713Formamide2×HCID 5003444Sodium cyanoborohydride2×HCID 210909885-[4-(Benzyloxy)phenyl]-1-(4-methoxyphenyl)-1H-pyrazol-3-amine

Product 1

HCID 210909945-[4-(Benzyloxy)phenyl]-1-(4-methoxyphenyl)-N,N-dimethyl-1H-pyrazol-3-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

37% Aqueous formamide solution (6 ml) and sodium cyanoborohydride (1.39 g) were added successively to a solution of 5-[4-(benzyloxy)phenyl]-1-(4-methoxyphenyl)-1H-pyrazol-3-amine obtained by Example 14-2 (2.75 g) in methanol 30 ml. The reaction mixture was stirred at room temperature for 3 days, occasionally adding 37% aqueous formamide solution and sodium cyanoborohydride appropriate amount to consume all starting material.

Workup

  1. customto consume all starting material

Sources & evidence

ORD record
ord-3cc1309e781d4f95aa1c54fd2212ee6b
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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