Anthranilamide → HCID 67298039, compound

HRID 1520361Notes

Reaction equation

HRID 1520361 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([OH:9])=O)=[CH:3][N:2]=1.[NH2:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([NH2:15])=[O:14].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[C:13]([C:12]1[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=1[NH:10][C:7]([C:4]1[CH:5]=[CH:6][N:1]=[N:2][CH:3]=1)=[O:9])(=[O:14])[NH2:15]

Participants

6

Reactant 4

HCID 6942AnthranilamideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 2761046Pyridazine-4-carboxylic Acid

Product 1

HCID 67298039HCID 67298039, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of pyridazine-4-carboxylic acid (500 mg, 4.0 mmol, 1.0 eq.), 2-aminobenzamide (603 mg, 4.4 mmol, 1.1 eq.) and HBTU (3.0 g, 8.0 mmol, 2.0 eq.) was suspended in 15 mL of DMF. DIPEA (2.0 mL, 1.56 g, 12.0 mmol, 3.0 eq.) was added dropwise at room temperature and was stirred over night. After quenching with water, the resulting precipitate was collected and washed with a small amount of DCM. A white solid (388 mg) was obtained, LCMS m/z=243.1 (M+1) (Method B) (retention time=0.99 min) was used in the next step without further purification.

Workup

  1. customAfter quenching with water
  2. customthe resulting precipitate was collected
  3. washwashed with a small amount of DCM

Sources & evidence

ORD record
ord-cc069d1992454b0aa459460f6c07fecd
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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