2,6-Dichlorobenzoyl chloride → HCID 44569945, compound

HRID 886719Notes

Reaction equation

HRID 886719 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14]([NH:16][CH2:17][C:18]([CH2:24][NH:25][CH2:26][CH3:27])([OH:23])[C:19]([F:22])([F:21])[F:20])=[O:15].C(N(C(C)C)CC)(C)C.[Cl:37][C:38]1[CH:46]=[CH:45][CH:44]=[C:43]([Cl:47])[C:39]=1[C:40](Cl)=[O:41]>O1CCCC1>[C:18]([O-:41])(=[O:23])[CH3:24].[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=2)[N:5]=[CH:4][C:3]=1[C:14]([NH:16][CH2:17][C:18]([CH2:24][N:25]([C:40]([C:39]1[C:38]([Cl:37])=[CH:46][CH:45]=[CH:44][C:43]=1[Cl:47])=[O:41])[CH2:26][CH3:27])([OH:23])[C:19]([F:22])([F:21])[F:20])=[O:15]

Participants

6

Reactant 3

HCID 783922,6-Dichlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 59187223HCID 59187223, compound

Product 2

HCID 175AcetateHCID 44569945HCID 44569945, compoundYield 174.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-amino-N-{2-[(ethylamino)methyl]-3,3,3-trifluoro-2-hydroxypropyl}-1-(4-fluorophenyl)-1H-pyrazole-4-carboxamide (56 mg, 0.15 mmol) in anhydrous tetrahydrofuran (2 ml) cooled in ice was added diisopropylethylamine (0.052 ml, 0.3 mmol) followed by 2,6-dichlorobenzoyl chloride (0.023 ml, 0.164 mmol). After 20 minutes, the mixture was removed from the ice and left at 21° C. for 19 hours. The mixture was blown down, the residue was dissolved in dichloromethane (3 ml) and washed with 2M hydrochloric acid (1 ml) and water (1 ml). It was again blown down and purified on a 5 g SPE cartridge, eluting with dichloromethane and then mixtures of cyclohexane/ethyl:acetate (10:1), (5:1), (3:1) and finally (2:1) to give the title compound (73.5 mg).

Workup

  1. customthe mixture was removed from the ice
  2. waitleft at 21° C. for 19 hours
  3. dissolutionthe residue was dissolved in dichloromethane (3 ml)
  4. washwashed with 2M hydrochloric acid (1 ml) and water (1 ml)
  5. custompurified on a 5 g SPE cartridge
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-f517fddd12df427680613823ce8a76f5
Source dataset
uspto-grants-2012_08
Patent number
US08247377B2

Reaction notes

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