Hydrazine → HCID 57656177, compound

HRID 911551Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([S:20][CH2:21][CH2:22][CH2:23][N:24]3C(=O)C4C(=CC=CC=4)C3=O)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].NN>C(O)C>[NH2:24][CH2:23][CH2:22][CH2:21][S:20][C:15]1[C:12]2[CH2:13][CH2:14][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:9][CH2:10][C:11]=2[CH:18]=[CH:17][C:16]=1[Cl:19]

Participants

Conditions

Temperature: 65 °C

Procedure

Suspend 3-tert-butoxycarbonyl-7-chloro-6-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-propylthio]-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1.20 g, 2.39 mmol) in ethanol (53.2 mL), add hydrazine (0.150 mL, 4.78 mmol) and heat at 65° C. for 2 h. Cool to ambient temperature, filter from precipitate, and concentrate in vacuo to provide the 6-(3-aminopropylthio)-3-tert-butoxycarbonyl-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (861 mg, 97%). MS (APCI+) m/z: 371 (M+H)+.

Workup

temperatureCool to ambient temperature
filtrationfilter from precipitate
concentrationconcentrate in vacuo

Sources & evidence

ORD record: ord-c0a5ae7cfcb24543a64724ca0d3fb48c
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022062B2

Reaction notes

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