Isopropylamine → HCID 18446929, compound

HRID 1983072Notes

Reaction equation

HRID 1983072 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].[Cl:5][C:6]1[C:7]([N:12]2[C:16]([C:17]3[O:22][C:21](=[O:23])[C:20]4[CH:24]=[C:25]([N+:29]([O-:31])=[O:30])[CH:26]=[C:27]([CH3:28])[C:19]=4[N:18]=3)=[CH:15][C:14]([C:32]([F:35])([F:34])[F:33])=[N:13]2)=[N:8][CH:9]=[CH:10][CH:11]=1>O1CCOCC1>[Cl:5][C:6]1[C:7]([N:12]2[C:16]([C:17]([NH:18][C:19]3[C:20]([C:21]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:23])=[CH:24][C:25]([N+:29]([O-:31])=[O:30])=[CH:26][C:27]=3[CH3:28])=[O:22])=[CH:15][C:14]([C:32]([F:35])([F:34])[F:33])=[N:13]2)=[N:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 690644832-[1-(3-Chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]-8-methyl-6-nitro-4H-3,1-benzoxazin-4-one

Product 1

HCID 18446929HCID 18446929, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Isopropyl amine (0.35 mL, 4.11 mmol) was added to a solution of 619 mg (1.37 mmol) of the product of Step B in dioxane (8 mL) at 25° C. After being stirred overnight, the resulting heterogenous mixture was concentrated and the residue was triturated with methanol (10 mL). Filtration gave 100 mg of the title product. The filtrate was concentrated and the resulting residue was triturated with diethyl ether. Filtration of the resulting solid provided an additional 320 mg of the title product, m.p. 170-172° C.

Workup

  1. concentrationthe resulting heterogenous mixture was concentrated
  2. customthe residue was triturated with methanol (10 mL)
  3. filtrationFiltration

Sources & evidence

ORD record
ord-884240302a6a4e819bbe11983f6cd039
Source dataset
uspto-grants-2009_06
Patent number
US07541377B2

Reaction notes

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