Hydrochloric Acid → HCID 11682846, compound

HRID 2240260Notes

Reaction equation

HRID 2240260 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[NH:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][C:13]=2[F:19])[NH:4][CH:3]=1.[Cl:20][C:21]1[CH:26]=[C:25](Cl)[N:24]=[C:23]([NH2:28])[N:22]=1.Cl.[OH-].[Na+]>O>[Cl:20][C:21]1[N:22]=[C:23]([NH2:28])[N:24]=[C:25]([NH:18][C:15]2[CH:16]=[CH:17][C:12]([NH:11][C:9]3[CH:8]=[CH:7][N:6]=[C:5]4[NH:4][CH:3]=[C:2]([Cl:1])[C:10]=34)=[C:13]([F:19])[CH:14]=2)[CH:26]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 655222-Amino-4,6-dichloropyrimidineHCID 59305024HCID 59305024, compound

Product 1

HCID 11682846HCID 11682846, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

57 mg (210 mmol) of N1-(3-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)-2-fluorobenzene-1,4-diamine and 47 mg (290 μmol) of 4,6-dichloropyrimidine-2-amine are suspended in 5 ml of water. 290 μl (290 mmol) of 1 M hydrochloric acid are added, and the mixture is stirred at 100° C. overnight. Using 1N aqueous sodium hydroxide solution, the suspension is then adjusted to pH 10, resulting in the precipitation of crystals. The solid is filtered off and washed with water. The crude product is purified by column chromatography on silica gel (mobile phase: dichloromethane/methanol (7M ammonia) 100:1 to 10:1) and subsequent preparative RP-HPLC.

Workup

  1. customresulting in the precipitation of crystals
  2. filtrationThe solid is filtered off
  3. washwashed with water
  4. customThe crude product is purified by column chromatography on silica gel (mobile phase: dichloromethane/methanol (7M ammonia) 100:1 to 10:1) and subsequent preparative RP-HPLC

Sources & evidence

ORD record
ord-b6127d2476354fc199f20c36e8071d1d
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

Loading…