Ethanolamine → HCID 117988196, compound

HRID 2206204Notes

Reaction equation

HRID 2206204 reaction equation
[Cl:1][C:2]1[C:3]2[N:12]([C:13]3[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=3[F:20])[N:11]=[C:10]([C:21]3[CH:29]=[CH:28][C:24]([C:25]([OH:27])=O)=[CH:23][CH:22]=3)[C:4]=2[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[NH2:30][CH2:31][CH2:32][OH:33].C(N(CC)CC)C.O>CN(C=O)C>[Cl:1][C:2]1[C:3]2[N:12]([C:13]3[C:14]([F:20])=[CH:15][CH:16]=[CH:17][C:18]=3[F:19])[N:11]=[C:10]([C:21]3[CH:22]=[CH:23][C:24]([C:25]([NH:30][CH2:31][CH2:32][OH:33])=[O:27])=[CH:28][CH:29]=3)[C:4]=2[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 962WaterHCID 8471TriethylamineHCID 117988151HCID 117988151, compound

Product 1

HCID 117988196HCID 117988196, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(7-chloro-1-(2,6-difluorophenyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)benzoic acid (100 mg) obtained in Step A of Example 231, 2-aminoethanol (0.022 mL) and triethylamine (0.050 mL) in DMF (3 mL) was added 2-(7-azabenzotriazol-1-yl)-1,1,3,3-hexafluorophosphate (137 mg), and the mixture was stirred overnight at room temperature. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (105 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2bdf9d2511674ce3b7a8613cf7e79a47
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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