Isopropylamine → HCID 178492664, compound

HRID 245635Notes

Reaction equation

HRID 245635 reaction equation
[Br:1][C:2]1[C:6]2=[CH:7][C:8]([Cl:30])=[C:9]3[C:14]([C:13](=[O:15])[O:12][C:11]([C:16]4[N:17]([C:23]5[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][N:24]=5)[N:18]=[C:19]([O:21][CH3:22])[CH:20]=4)=[N:10]3)=[C:5]2[NH:4][N:3]=1.C(#N)C.O.[CH:35]([NH2:38])([CH3:37])[CH3:36]>[Cl-].[Na+].O>[CH:35]([NH:38][C:13]([C:14]1[C:9]([NH:10][C:11]([C:16]2[N:17]([C:23]3[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][N:24]=3)[N:18]=[C:19]([O:21][CH3:22])[CH:20]=2)=[O:12])=[C:8]([Cl:30])[CH:7]=[C:6]2[C:5]=1[NH:4][N:3]=[C:2]2[Br:1])=[O:15])([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 18373917Acetonitrile--water (1/1)HCID 178487785HCID 178487785, compound

Product 1

HCID 178492664HCID 178492664, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a suspension of 120 mg (0.24 mmol) of the above 3-bromo-5-chloro-7-[2-(3-chloro-pyridin-2-yl)-5-methoxy-2H-pyrazol-3-yl]-1H-8-oxa-1,2,6-triaza-cyclopenta[a]naphthalen-9-one in 2.4 mL of a mixture acetonitrile:H2O 4:2 (v/v) is added 60 μL (0.71 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 1:2) affords 56 mg (42%) of a white solid; LC/MS:568/570 (M+H)+, m.p.: 217-218° 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 1:2)

Sources & evidence

ORD record
ord-c7ee2d0680cc4ebda3aaec56715afc5c
Source dataset
uspto-grants-2014_02
Patent number
US08658801B2

Reaction notes

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