5-(4,6-dimethyl-1H-benzimidazol-2-yl)-4-methyl-N-[3-(1-methyl-4-piperidinyl)propyl]-2-pyrimidinamine 2,3-dihydroxybutanedioate → 5-(4,6-dimethyl-1H-benzimidazol-2-yl)-4-methyl-N-[3-(1-methyl-4-piperidinyl)-propyl]-2-pyrimidinamine 2,3-dihydroxybutanedioate hydrate

HRID 57124Notes

Reaction equation

HRID 57124 reaction equation
[OH:1][CH:2]([CH:6]([OH:10])[C:7]([OH:9])=[O:8])[C:3]([OH:5])=[O:4].[CH3:11][C:12]1[C:20]2[N:19]=[C:18]([C:21]3[C:22]([CH3:38])=[N:23][C:24]([NH:27][CH2:28][CH2:29][CH2:30][CH:31]4[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]4)=[N:25][CH:26]=3)[NH:17][C:16]=2[CH:15]=[C:14]([CH3:39])[CH:13]=1>CC1C2N=C(C3C(C)=NC(NCCCC4CCN(C)CC4)=NC=3)NC=2C=C(C)C=1.O>[OH2:1].[OH:1][CH:2]([CH:6]([OH:10])[C:7]([OH:9])=[O:8])[C:3]([OH:5])=[O:4].[CH3:11][C:12]1[C:20]2[N:19]=[C:18]([C:21]3[C:22]([CH3:38])=[N:23][C:24]([NH:27][CH2:28][CH2:29][CH2:30][CH:31]4[CH2:32][CH2:33][N:34]([CH3:37])[CH2:35][CH2:36]4)=[N:25][CH:26]=3)[NH:17][C:16]=2[CH:15]=[C:14]([CH3:39])[CH:13]=1

Participants

4

Reactant 1

HCID 903887025-(4,6-dimethyl-1H-benzimidazol-2-yl)-4-methyl-N-[3-(1-methyl-4-piperidinyl)propyl]-2-pyrimidinamine 2,3-dihydroxybutanedioate

Product 1

HCID 862756685-(4,6-dimethyl-1H-benzimidazol-2-yl)-4-methyl-N-[3-(1-methyl-4-piperidinyl)-propyl]-2-pyrimidinamine 2,3-dihydroxybutanedioate hydrate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 23650961ToreforantSolvent

Procedure

In a glass tube with magnetic stirring bar, (5-(4,6-dimethyl-1H-benzimidazol-2-yl)-4-methyl-N-[3-(1-methyl-4-piperidinyl)propyl]-2-pyrimidinamine 2,3-dihydroxybutanedioate (1:0.5)), compound 2.1 (crude) was dissolved in water at 60° C. The solution was cooled to room temperature, then stirred overnight. A yellowish suspension formed. After cooling the reaction mixture to 2.5° C. for 1.5 h, the solid was isolated by filtration and washed with water to provide 5-(4,6-dimethyl-1H-benzimidazol-2-yl)-4-methyl-N-[3-(1-methyl-4-piperidinyl)-propyl]-2-pyrimidinamine 2,3-dihydroxybutanedioate hydrate (1:0.5:4), Compound 3.S.

Workup

  1. customA yellowish suspension formed
  2. temperatureAfter cooling the reaction mixture to 2.5° C. for 1.5 h
  3. customthe solid was isolated by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-d651722778814401bf6b2185c694d7c4
Source dataset
uspto-grants-2016_09
Patent number
US09434715B2

Reaction notes

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