Isopropylamine → HCID 178434361, compound

HRID 245639Notes

Reaction equation

HRID 245639 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:31]([CH3:32])=[N:30][NH:29][C:5]2=[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].C(#N)C.O.[CH:37]([NH2:40])([CH3:39])[CH3:38]>[Cl-].[Na+].O>[CH:37]([NH:40][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:20])([F:19])[F:18])[CH:16]=2)=[O:8])=[C:2]([Cl:1])[CH:3]=[C:4]2[C:5]=1[NH:29][N:30]=[C:31]2[CH3:32])=[O:28])([CH3:39])[CH3:38]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 18373917Acetonitrile--water (1/1)HCID 1784341745-chloro-7-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-3-methyl-1H-8-oxa-1,2,6-triaza-cyclopenta[a]naphthalen-9-one

Product 1

HCID 178434361HCID 178434361, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a suspension of 148 mg (0.20 mmol) of the above 5-chloro-7-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-3-methyl-1H-8-oxa-1,2,6-triaza-cyclopenta[a]naphthalen-9-one in 5.92 mL of a mixture acetonitrile: H2O 4:1 (v/v) is added 51 μL (0.60 mmol) of isopropylamine. The reaction mixture is stirred for 6 hours at ambient temperature. Brine is then added to the mixture and the product is extracted with ethyl acetate (3 times). The regrouped organic phases are dried on Na2SO4, filtrated and evaporated. The purification of the residue by flash chromatography (SiO2, heptane/ethyl acetate 1:1) affords 30 mg (28%) of a white solid; LC/MS:540/542 (M+H)+, m.p.: 235-236° C.

Workup

  1. extractionthe product is extracted with ethyl acetate (3 times)
  2. customThe regrouped organic phases are dried on Na2SO4
  3. filtrationfiltrated
  4. customevaporated
  5. customThe purification of the residue by flash chromatography (SiO2, heptane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-3e194bb5849e4ddca4ab72fa94daab57
Source dataset
uspto-grants-2014_02
Patent number
US08658801B2

Reaction notes

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