Ethanolamine → HCID 19966994, compound

HRID 976279Notes

Reaction equation

HRID 976279 reaction equation
[F:1][C:2]([F:29])([O:6][C:7]1[CH:8]=[C:9]([NH:13][C:14]2[N:19]=[C:18]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([C:26](O)=[O:27])[CH:21]=3)[CH:17]=[CH:16][N:15]=2)[CH:10]=[CH:11][CH:12]=1)[CH:3]([F:5])[F:4].Cl.C(N=C=NCCCN(C)C)C.ON1C(=O)CCC1=O.[CH2:50]([CH2:52][NH2:53])[OH:51]>CN(C=O)C.C(OCC)(=O)C>[F:29][C:2]([F:1])([O:6][C:7]1[CH:8]=[C:9]([NH:13][C:14]2[N:19]=[C:18]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([C:26]([NH:53][CH2:52][CH2:50][OH:51])=[O:27])[CH:21]=3)[CH:17]=[CH:16][N:15]=2)[CH:10]=[CH:11][CH:12]=1)[CH:3]([F:5])[F:4]

Participants

7

Reactant 4

HCID 700EthanolamineHCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19966941HCID 19966941, compound

Product 1

HCID 19966994HCID 19966994, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

100 mg (0.2 mmol) of N-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-4-(2-carboxy-4-pyridyl)-2-pyrimidineamine, 73 mg (0.38 mmol) of N-ethyl-N'-(3-dimethylaminopropyl)-carbodiimide hydrochloride and 44 mg (0.38 mmol) of N-hydroxysuccinimide are dissolved in 3 ml of dimethyflormamide and stirred for 2.5 h at RT. The reaction mixture is then added dropwise at 0° over a period of 30 minutes to a solution of 0.75 ml (12.3 mmol) of ethanolamine in 2 ml of DMF. After stirring for 14 h at RT, the reaction mixture is poured into 50 ml of ethyl acetate and extracted with aqueous sodium chloride solution (30 ml) and pH 7 buffer (30 ml), and the organic phase is dried (sodium sulfate) and concentrated. Crystallisation from THF/diethyl ether gives N-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-4-[2-(2-hydroxy-ethyl-aminocarbonyl)-4-pyridyl]-2-pyrimidineamine; m.p. 159°, FAB-MS: 452 (M+ +H).

Workup

  1. stirringAfter stirring for 14 h at RT
  2. extractionextracted with aqueous sodium chloride solution (30 ml) and pH 7 buffer (30 ml)
  3. dry with materialthe organic phase is dried (sodium sulfate)
  4. concentrationconcentrated
  5. customCrystallisation from THF/diethyl ether

Sources & evidence

ORD record
ord-713bf26659b849ae820f9ec1120485bf
Source dataset
uspto-grants-1997_03
Patent number
US05612340

Reaction notes

Loading…