Ethyl Acetate → HCID 178496377, compound

HRID 1695591Notes

Reaction equation

HRID 1695591 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[CH:10]([NH:12][C:13]1[O:14][CH2:15][C:16]3[CH:22]=[C:21]([NH2:23])[CH:20]=[CH:19][C:17]=3[N:18]=1)[CH2:9]C2.[CH3:24][O:25][CH2:26][C:27](Cl)=[O:28].C(OCC)(=[O:32])C>C(=O)([O-])O.[Na+]>[CH3:24][O:25][CH2:26][C:27]([NH:23][C:21]1[CH:20]=[CH:19][C:17]2[N:18]=[C:13]([NH:12][CH:10]3[C:11]4[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=4[O:32][CH2:9]3)[O:14][CH2:15][C:16]=2[CH:22]=1)=[O:28]

Participants

5

Reactant 3

HCID 8857Ethyl Acetate2×HCID 96623Methoxyacetyl chlorideHCID 178488335HCID 178488335, compound

Product 1

HCID 178496377HCID 178496377, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of rac-N2-(7-methoxy-indan-1-yl)-4H-benzo[d][1,3]oxazine-2,6-diamine (Example 10) (100 mg, 0.321 mmol) in ethyl acetate (5 ml) and sat. sodium hydrogen carbonate-sol. at 0° C. was added methoxyacetyl chloride (35 ul, 0.385 mmol) and the mixture was stirred at 23° C. for 16 h. Diluted with ethyl acetate, washed with water, dried the organic layer over sodium sulfate. After filtration, the solvent was removed in vacuum and the crude product was triturated with diethyl ether to give the title compound as a white solid (90 mg, 73%), MS (ISP) m/e=384.2 [(M+H)+].

Workup

  1. washwashed with water
  2. dry with materialdried the organic layer over sodium sulfate
  3. filtrationAfter filtration
  4. customthe solvent was removed in vacuum
  5. customthe crude product was triturated with diethyl ether

Sources & evidence

ORD record
ord-bfd3456c1e7241d1bd3f1d0a4da9ab5f
Source dataset
uspto-grants-2012_04
Patent number
US08163740B2

Reaction notes

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