1-Isopropylhydrazine hydrochloride → 10-chloro-2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[4,3-f][1,4]oxazepine

HRID 886026Notes

Reaction equation

[Cl:1][C:2]1[N:12]=[CH:11][C:10]2[O:9][CH2:8][CH2:7][N:6]3[CH:13]=[C:14]([C:16]([N:18]=[CH:19][N:20](C)C)=O)[N:15]=[C:5]3[C:4]=2[CH:3]=1.Cl.[CH:24]([NH:27]N)([CH3:26])[CH3:25]>C(O)(=O)C>[Cl:1][C:2]1[N:12]=[CH:11][C:10]2[O:9][CH2:8][CH2:7][N:6]3[CH:13]=[C:14]([C:16]4[N:27]([CH:24]([CH3:26])[CH3:25])[N:20]=[CH:19][N:18]=4)[N:15]=[C:5]3[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 660 mg (2.06 mmol) of 10-chloro-N-((dimethylamino)methylene)-5,6-dihydroimidazo[1,2-d]pyrido[4,3-f][1,4]oxazepine-2-carboxamide and isopropylhydrazine hydrochloride (0.332 g, 3.00 mmol) in 44 ml of acetic acid was heated at 85° C. for 3 hours. The mixture was cooled, filtered and mixed with 15 ml of water. A precipitate was filtered out, washed with water and dried in high vacuum. The above solid was triturated with 10 ml of ethyl acetate, filtered out, washed with ethyl acetate, ethyl ether and dried on air. Yield 0.710 g. MS: 331.2. 1H NMR (500 MHz, DMSO) δ 8.26 (s, 1H), 8.20 (s, 1H), 8.11 (s, 1H), 7.96 (s, 1H), 5.76 (dt, J=13.1, 6.6, 1H), 4.62 (q, J=5.6, 4H), 1.50 (d, J=6.6, 6H).

Workup

temperatureThe mixture was cooled
filtrationfiltered
additionmixed with 15 ml of water
filtrationA precipitate was filtered out
washwashed with water
customdried in high vacuum
customThe above solid was triturated with 10 ml of ethyl acetate
filtrationfiltered out
washwashed with ethyl acetate, ethyl ether
customdried on air

Sources & evidence

ORD record: ord-a263e370ebc24c88991517b0fff6475a
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242104B2

Reaction notes

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