2-(1H-pyrrol-1-yl)benzaldehyde → N4-(1-(2-(1H-Pyrrol-1-yl)benzyl)piperidin-4-yl)-N2-(3-(dimethylamino)propyl)quinazoline-2,4-diamine

HRID 215922Notes

Reaction equation

HRID 215922 reaction equation
[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][CH2:5][NH:6][C:7]1[N:16]=[C:15]([NH:17][CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1.[N:25]1([C:30]2[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=2[CH:32]=O)[CH:29]=[CH:28][CH:27]=[CH:26]1.[BH3-]C#N.[Na+]>CO.[Cl-].[Cl-].[Zn+2]>[N:25]1([C:30]2[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=2[CH2:32][N:21]2[CH2:20][CH2:19][CH:18]([NH:17][C:15]3[C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[N:8]=[C:7]([NH:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:24])[N:16]=3)[CH2:23][CH2:22]2)[CH:26]=[CH:27][CH:28]=[CH:29]1

Participants

6

Reactant 3

HCID 49612592-(1H-pyrrol-1-yl)benzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 58006203N2-(3-(Dimethylamino)propyl)-N4-(piperidin-4-yl)quinazoline-2,4-diamine

Product 1

HCID 58006247N4-(1-(2-(1H-Pyrrol-1-yl)benzyl)piperidin-4-yl)-N2-(3-(dimethylamino)propyl)quinazoline-2,4-diamine

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

N2-(3-(Dimethylamino)propyl)-N4-(piperidin-4-yl)quinazoline-2,4-diamine (62 mg, 0.189 mmol), 2-(1H-pyrrol-1-yl)benzaldehyde (32 mg, 0.189 mmol), NaCNBH3 (12 mg, 0.190 mmol) and ZnCl2 (13 mg, 0.09 mmol) in MeOH (1 ml) was stirred at room temperature overnight. The solvent was removed under reduced pressure, and the crude product was purified by silica gel chromatography using 5% NH3 ca. 7 N MeOH in CH2Cl2 and 90% CH2Cl2 solution as eluent to produce the title compound as a brown oil.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5378b0a46d514d1dad5b383f27eb4f9c
Source dataset
uspto-grants-2012_06
Patent number
US08193203B2

Reaction notes

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