Cyclopropanecarbonyl chloride → HCID 178489486, compound

HRID 1695583Notes

Reaction equation

HRID 1695583 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[CH2:5][NH:6][C:7]1[O:8][CH2:9][C:10]2[CH:16]=[C:15]([NH2:17])[CH:14]=[CH:13][C:11]=2[N:12]=1.[CH:22]1([C:25](Cl)=[O:26])[CH2:24][CH2:23]1>C(OCC)(=O)C.C(=O)([O-])O.[Na+].O>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[CH2:5][NH:6][C:7]1[O:8][CH2:9][C:10]2[CH:16]=[C:15]([NH:17][C:25]([CH:22]3[CH2:24][CH2:23]3)=[O:26])[CH:14]=[CH:13][C:11]=2[N:12]=1

Participants

6

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 178489485HCID 178489485, compound

Product 1

HCID 178489486HCID 178489486, compoundYield 60.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
23 °C

Procedure

To a vigorously stirred solution of N2-(2-methoxy-benzyl)-4H-benzo[d][1,3]oxazine-2,6-diamine (Example 4) (128 mg, 0.45 mmol; HPLC 0.41 min) in ethyl acetate (2 ml) and sat. sodium hydrogen carbonate-sol. (1.2 ml) at 23° C. was dropwise added cyclopropanecarbonyl chloride (50 ul, 0.54 mmol) and the mixture was stirred at 23° C. for 20 min. Diluted with ethyl acetate and water, separated phases, washed organic layer with brine and dried over sodium sulfate. Removal of the solvent in vacuum left an off-white solid which was purified by silica gel column chromatography with heptane/ethyl acetate 1:1 to 0:1 followed by trituration with diethyl ether to give the title compound as a white solid (95 mg, 55%, HPLC 0.998 min 100%), MS (ISP) m/e=352.3 [(M+H)+].

Workup

  1. customat 23° C.
  2. customseparated phases
  3. washwashed organic layer with brine
  4. dry with materialdried over sodium sulfate
  5. customRemoval of the solvent in vacuum
  6. waitleft an off-white solid which
  7. customwas purified by silica gel column chromatography with heptane/ethyl acetate 1:1 to 0:1

Sources & evidence

ORD record
ord-2971abd91032456ab3258f42c7e6304c
Source dataset
uspto-grants-2012_04
Patent number
US08163740B2

Reaction notes

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