Ammonia → HCID 86693521, compound

HRID 575458Notes

Reaction equation

HRID 575458 reaction equation
[I:1][C:2]1[CH:20]=[CH:19][C:5]2[O:6][CH2:7][CH2:8][C:9]3[N:10]([N:11]=[C:12]([C:14](OCC)=[O:15])[CH:13]=3)[C:4]=2[CH:3]=1.[NH3:21]>>[I:1][C:2]1[CH:20]=[CH:19][C:5]2[O:6][CH2:7][CH2:8][C:9]3[N:10]([N:11]=[C:12]([C:14]([NH2:21])=[O:15])[CH:13]=3)[C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 86693520HCID 86693520, compound

Product 1

HCID 86693521HCID 86693521, compoundYield 36%

Conditions

Temperature
130 °C

Procedure

A suspension of ethyl 9-iodo-4,5-dihydrobenzo[b]pyrazolo[1,5-d][1,4]oxazepine-2-carboxylate (300 mg, 0.78 mmol) in 7 M ammonia solution (in methanol, 3 ml) was heated in a microwave apparatus to 130° C. for 70 minutes. After cooling the volatiles were removed in vacuo and the residue was purified by FCC (silica, 20-100% ethyl acetate in heptane) to give 99 mg (36%) of the title compound as an off-white solid. 1H NMR (DMSO, 500 MHz) δ 3.17 (2H, t, J=5.8 Hz), 4.47 (2H, t, J=5.9 Hz), 6.71 (1H, s), 7.03 (1H, d, J=8.5 Hz), 7.36 (1H, s), 7.66 (1H, dd, J=8.5, 2.2 Hz), 7.81 (1H, s), 8.29 (1H, d, J=2.2 Hz); M+1=356

Workup

  1. temperatureAfter cooling the volatiles
  2. customwere removed in vacuo
  3. customthe residue was purified by FCC (silica, 20-100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-6989ad0e728745fbbb3c51c72d406305
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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