Sodium Hydroxide → HCID 56646549, compound

HRID 1773608Notes

Reaction equation

HRID 1773608 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH2:10][C:11]2[O:15][C:14]([Si](C(C)C)(C(C)C)C(C)C)=[N:13][CH:12]=2)=[C:6]([NH2:8])[CH:7]=1.[N:26]1[N:30]2[CH:31]=[CH:32][CH:33]=[N:34][C:29]2=[C:28]([C:35](O)=[O:36])[CH:27]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH2:10][C:11]2[O:15][CH:14]=[N:13][CH:12]=2)=[C:6]([NH:8][C:35]([C:28]2[CH:27]=[N:26][N:30]3[CH:31]=[CH:32][CH:33]=[N:34][C:29]=23)=[O:36])[CH:7]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 1910189Pyrazolo[1,5-a]pyrimidine-3-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58056088HCID 58056088, compound

Product 1

HCID 56646549HCID 56646549, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Chloro-2-(2-triisopropylsilanyl-oxazol-5-ylmethoxy)-phenylamine was coupled with pyrazolo[1,5-a]pyrimidine-3-carboxylic acid in presence of HBTU as described in Example 1. The product was deprotected by heating with an aqueous solution of sodium hydroxide in methanol for 2 hours. The reaction mixture was cooled; the solid formed was collected by filtration and washed with water. The crude residue was purified by flash chromatography to give 18 mg of pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [5-chloro-2-(oxazol-5-ylmethoxy)-phenyl]-amide as an off-white solid. MS=370 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solid formed
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-f6b6b7ac26b346cbaeb7636c742c0ecd
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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