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

HRID 215924Notes

Reaction equation

HRID 215924 reaction equation
[CH2:1]([N:3]([CH2:25][CH3:26])[CH2:4][CH2:5][CH2:6][NH:7][C:8]1[N:17]=[C:16]([NH:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)[CH3:2].CN(C)CCCNC1N=C(NC2CCNCC2)C2C(=CC=CC=2)N=1.[N:51]1([C:56]2[CH:63]=[CH:62][CH:61]=[CH:60][C:57]=2[CH:58]=O)[CH:55]=[CH:54][CH:53]=[CH:52]1.[BH3-]C#N.[Na+]>CO.[Cl-].[Cl-].[Zn+2]>[N:51]1([C:56]2[CH:63]=[CH:62][CH:61]=[CH:60][C:57]=2[CH2:58][N:22]2[CH2:23][CH2:24][CH:19]([NH:18][C:16]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[N:9]=[C:8]([NH:7][CH2:6][CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[CH2:25][CH3:26])[N:17]=3)[CH2:20][CH2:21]2)[CH:52]=[CH:53][CH:54]=[CH:55]1

Participants

7

Reactant 4

HCID 49612592-(1H-pyrrol-1-yl)benzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 58006203N2-(3-(Dimethylamino)propyl)-N4-(piperidin-4-yl)quinazoline-2,4-diamineHCID 67027548N2-(3-(diethylamino)propyl)-N4-(piperidin-4-yl)quinazoline-2,4-diamine

Product 1

HCID 58006140N4-(1-(2-(1H-Pyrrol-1-yl)benzyl)piperidin-4-yl)-N2-(3-(diethylamino)propyl)quinazoline-2,4-diamine

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

A solution of 56 mg (0.155 mmol) N2-(3-(diethylamino)propyl)-N4-(piperidin-4-yl)quinazoline-2,4-diamine (prepared analogously to Compound 129) 2-(1H-pyrrol-1-yl)benzaldehyde (27 mg, 0.157 mmol), NaCNBH3 (10 mg, 0.160 mmol) and ZnCl2 (11 mg, 0.08 mmol) in MeOH (1 ml) was stirred at room temperature overnight to obtain the target compound.

Workup

  1. customto obtain the target compound

Sources & evidence

ORD record
ord-9ef2bdd6ffff4fbc9f1ded1876e2551b
Source dataset
uspto-grants-2012_06
Patent number
US08193203B2

Reaction notes

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