Ammonium Hydroxide → HCID 86693530, compound

HRID 575465Notes

Reaction equation

HRID 575465 reaction equation
[I:1][C:2]1[CH:22]=[CH:21][C:5]2[O:6][CH2:7][C:8]3([C:11]4[N:12]([N:13]=[C:14]([C:16](OCC)=[O:17])[CH:15]=4)[C:4]=2[CH:3]=1)[CH2:10][CH2:9]3.[OH-].[NH4+:24]>O1CCOCC1.C(OCC)(=O)C.O>[I:1][C:2]1[CH:22]=[CH:21][C:5]2[O:6][CH2:7][C:8]3([C:11]4[N:12]([N:13]=[C:14]([C:16]([NH2:24])=[O:17])[CH:15]=4)[C:4]=2[CH:3]=1)[CH2:10][CH2:9]3

Participants

6

Reactant 2

HCID 14923Ammonium HydroxideHCID 86693528HCID 86693528, compound

Product 1

HCID 86693530HCID 86693530, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of ethyl 9-iodo-5H-spiro[benzo[b]pyrazolo[1,5-d][1,4]oxazepine-4,1′-cyclopropane]-2-carboxylate (313 mg, 0.76 mmol) in ammonium hydroxide (3 mL) and dioxane (2 mL) was sealed in a 20 mL microwave vial and heated at 110° C. behind a blast shield. The mixture was cooled to room temperature, diluted with ethyl acetate and water and washed with sodium bicarbonate solution. The organics were dried over sodium sulfate and concentrated by rotoevaporation to give the titled compound which was used without purification in subsequent operations. 1H NMR (400 MHz, DMSO) δ 8.44 (d, J=2.1 Hz, 1H), 7.83 (br s, 1H), 7.61 (dd, J=8.5, 2.2 Hz, 1H), 7.33 (br s, 1H), 6.99 (d, J=8.5 Hz, 1H), 6.55 (s, 1H), 4.22 (s, 2H), 1.10-0.96 (m, 4H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with sodium bicarbonate solution
  3. dry with materialThe organics were dried over sodium sulfate
  4. concentrationconcentrated by rotoevaporation

Sources & evidence

ORD record
ord-c858523e52984d49a05ced712dc61c54
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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