Isopropylamine → 7-chloro-6-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-benzo[1,2,5]thiadiazole-5-carboxylic acid isopropylamide

HRID 2039609Notes

Reaction equation

HRID 2039609 reaction equation
[Cl:1][C:2]1[C:3]2[C:4](=[N:29][S:30][N:31]=2)[CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[N:13]([C:21]3[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][N:22]=3)[N:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1)[O:8][C:7]2=[O:28].[CH:32]([NH2:35])([CH3:34])[CH3:33]>C1COCC1>[CH:32]([NH:35][C:7]([C:6]1[C:11]([NH:10][C:9]([C:12]2[N:13]([C:21]3[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][N:22]=3)[N:14]=[C:15]([C:17]([F:19])([F:18])[F:20])[CH:16]=2)=[O:8])=[C:2]([Cl:1])[C:3]2[C:4]([CH:5]=1)=[N:29][S:30][N:31]=2)=[O:28])([CH3:34])[CH3:33]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 578559084-chloro-6-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-7-oxa-2-thia-1,3,5-triaza-cyclopenta[b]naphthalen-8-one

Product 1

HCID 578559057-chloro-6-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-benzo[1,2,5]thiadiazole-5-carboxylic acid isopropylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 25 mg (52 mmol) of 4-chloro-6-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-7-oxa-2-thia-1,3,5-triaza-cyclopenta[b]naphthalen-8-one in 0.5 ml of THF, is added dropwise 7 ml (77 mmol) of isopropylamine. The reaction is stirred for 18 hours at ambient temperature. Then, the solvent is evaporated and the residue is suspended in a mixture of hexanes and a minimum of EtOAc. After decantation the solid is washed with a minimum of hexanes and after drying 24.5 mg (45 mmol, 87%) of a slightly brown solid were obtained. LC/MS: 544/546 (M+1)+.

Workup

  1. customThen, the solvent is evaporated
  2. additionthe residue is suspended in a mixture of hexanes
  3. washAfter decantation the solid is washed with a minimum of hexanes
  4. customafter drying 24.5 mg (45 mmol, 87%) of a slightly brown solid
  5. customwere obtained

Sources & evidence

ORD record
ord-0555172a11174fba88b844c2b67f1ed6
Source dataset
uspto-grants-2013_11
Patent number
US08580785B2

Reaction notes

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