1,2-Dichloroethane → HCID 178507937, compound

HRID 1012064Notes

Reaction equation

HRID 1012064 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]([C:11]([OH:13])=O)=[N:8][NH:9][CH:10]=1.[NH2:19][C:20]1[C:27]([NH2:28])=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][OH:23].C(Cl)CCl.C1C=CC2N([OH:42])N=NC=2C=1>CN(C=O)C>[NH2:19][C:20]1[C:21]([CH2:22][OH:23])=[CH:24][CH:25]=[CH:26][C:27]=1[NH:28][C:11]([C:7]1[C:6]([NH:5][C:4](=[O:42])[C:3]2[C:14]([F:18])=[CH:15][CH:16]=[CH:17][C:2]=2[F:1])=[CH:10][NH:9][N:8]=1)=[O:13]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 1514188(2,3-Diaminophenyl)methanolHCID 178524951HCID 178524951, compound

Product 1

HCID 178507937HCID 178507937, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(2,6-difluorobenzylamino)-1H-pyrazole-3-carboxylic acid (1.0 g, 3.7 mmol) (Example 16D), 2,3-diaminobenzylalcohol (560 mg, 4.1 mmol), EDC (870 mg, 4.5 mmol) and HOBt (610 mg, 4.5 mmol) in DMF (20 ml) was stirred at ambient temperature for 18 h and then reduced in vacuo. The residue was partitioned between EtOAc and brine and the organic portion dried (MgSO4) and reduced in vacuo. The residue was purified by flash column chromatography [SiO2, EtOAc-hexane (1:1, 2:1)] to give 4-(2,6-difluoro-benzoylamino)-1H-pyrazole-3-carboxylic acid (2-amino-3-hydroxymethyl-phenyl)-amide (860 mg).

Workup

  1. customThe residue was partitioned between EtOAc and brine
  2. dry with materialthe organic portion dried (MgSO4)
  3. customThe residue was purified by flash column chromatography [SiO2, EtOAc-hexane (1:1, 2:1)]

Sources & evidence

ORD record
ord-efe63fe2d4624af4b2c09887eb217789
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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