Diisopropylethylamine → HCID 178492301, compound

HRID 1982949Notes

Reaction equation

HRID 1982949 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]([OH:13])=O)=[N:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([NH2:23])[C:19]([NH2:22])=[CH:20][CH:21]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][CH3:14])=[CH:17][C:18]=1[NH:23][C:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[NH:8][N:9]=1)=[O:13]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1534044-Methoxy-o-phenylenediamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178524942HCID 178524942, compound

Product 1

HCID 178492301HCID 178492301, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid Compound 1c (200 mg, 0.826 mmol), 4-methoxy-benzene-1,2-diamine Compound 19a (114 mg, 0.826 mmol), HATU (314 mg, 0.826 mmol) and DIPEA (213 mg, 1.652 mmol) in DMF (10 mL) was stirred and heated to 45° C. overnight. The mixture was diluted with AcOEt (60 mL) and washed with water. The organic layer was separated, dried and evaporated to give a brown solid residue. The residue was recrystallized with AcOEt/hexane mixture to give 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (2-amino-5-methoxy-phenyl)-amide Compound 19b (221 mg, 74% yield) as a light brown powder. MS m/z 362 (M+).

Workup

  1. washwashed with water
  2. customThe organic layer was separated
  3. customdried
  4. customevaporated
  5. customto give a brown solid residue
  6. customThe residue was recrystallized with AcOEt/hexane mixture

Sources & evidence

ORD record
ord-24acd1a7e7b34876bbe72a028e45cb28
Source dataset
uspto-grants-2009_06
Patent number
US07541367B2

Reaction notes

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