Ammonium Hydroxide → HCID 86647073, compound

HRID 1621920Notes

Reaction equation

HRID 1621920 reaction equation
[Cl:1][CH:2]([C:7]1[CH:8]=[C:9]([C:22]2[N:27]=[C:26]([CH3:28])[N:25]=[C:24]([N:29]([CH2:39][C:40]3[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=3)[CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=3)[N:23]=2)[C:10]([NH:13][C:14]2[CH:15]=[N:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[N:11][CH:12]=1)[C:3]([F:6])([F:5])[F:4].[OH-].[NH4+:49]>CC#N>[Cl:1][CH:2]([C:7]1[CH:8]=[C:9]([C:22]2[N:27]=[C:26]([CH3:28])[N:25]=[C:24]([N:29]([CH2:30][C:31]3[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=3)[CH2:39][C:40]3[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=3)[N:23]=2)[C:10]([NH:13][C:14]2[CH:15]=[N:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[N:11][CH:12]=1)[C:3]([F:4])([F:5])[F:6].[NH2:49][CH:2]([C:7]1[CH:8]=[C:9]([C:22]2[N:27]=[C:26]([CH3:28])[N:25]=[C:24]([N:29]([CH2:39][C:40]3[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=3)[CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=3)[N:23]=2)[C:10]([NH:13][C:14]2[CH:15]=[N:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[N:11][CH:12]=1)[C:3]([F:6])([F:5])[F:4]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 666117034-(5-(1-chloro-2,2,2-trifluoroethyl)-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Product 1

HCID 86647073HCID 86647073, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(5-(1-Chloro-2,2,2-trifluoroethyl)-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.177 g, 0.266 mmol) was dissolved in MeCN (6.00 mL) and saturated ammonium hydroxide aqueous solution (0.6 mL, 4.31 mmol) was added at room temperature and the mixture was stirred at the same temperature for 5 h. The reaction mixture was concentrated and the crude product was adsorbed onto silica gel and chromatographed through a silica gel column (100% DCM to 5% MeOH (w/NH3 in DCM) to obtain 4-(5-(1-amino-2,2,2-trifluoroethyl)-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine 4-(5-(1-chloro-2,2,2-trifluoroethyl)-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.165 g, 96%) as a brown foam.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customchromatographed through a silica gel column (100% DCM to 5% MeOH (w/NH3 in DCM)

Sources & evidence

ORD record
ord-f30985ef8490432c9bc6a0f457c642e7
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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