Sodium cyanoborohydride → N2-(3-(Diethylamino)propyl)-N4-(1-((1-methyl-1H-indol-7-yl)methyl)piperidin-4-yl)quinazoline-2,4-diamine

HRID 215926Notes

Reaction equation

HRID 215926 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].[CH3:27][N:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][C:35]=2[CH:37]=O)[CH:30]=[CH:29]1.[BH3-]C#N.[Na+]>CO.[Cl-].[Cl-].[Zn+2]>[CH2:25]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][NH:7][C:8]1[N:17]=[C:16]([NH:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:37][C:35]3[CH:34]=[CH:33][CH:32]=[C:31]4[C:36]=3[N:28]([CH3:27])[CH:29]=[CH:30]4)[CH2:21][CH2:20]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)[CH3:26]

Participants

6

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 110409791-methyl-1H-indole-7-carbaldehydeHCID 67027548N2-(3-(diethylamino)propyl)-N4-(piperidin-4-yl)quinazoline-2,4-diamine

Product 1

HCID 58006186N2-(3-(Diethylamino)propyl)-N4-(1-((1-methyl-1H-indol-7-yl)methyl)piperidin-4-yl)quinazoline-2,4-diamine

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

A solution of N2-(3-(diethylamino)propyl)-N4-(piperidin-4-yl)quinazoline-2,4-diamine (56 mg, 0.157 mmol), 1-methyl-1H-indole-7-carbaldehyde (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-d5c39c9a97fc4ad8b3cfeb04696a7abb
Source dataset
uspto-grants-2012_06
Patent number
US08193203B2

Reaction notes

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