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 1530401Notes

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 1 o 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 1 o ml of ethyl acetate
filtrationfiltered out
washwashed with ethyl acetate, ethyl ether
customdried on air

Sources & evidence

ORD record: ord-e0d2f7385d724966a01443f509a020f5
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090628B2

Reaction notes

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