Hydrazine hydrate (1:1) → HCID 10340512, compound

HRID 273317Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[CH2:5][N:6]1[C:14]2[CH:13]=[CH:12][C:11](=[O:15])[N:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]=2[CH:8]=[C:7]1[C:22]([O:24]CC)=O.O.[NH2:31][NH2:32]>C(OCCO)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[CH2:5][N:6]1[C:14]2[CH:13]=[CH:12][C:11](=[O:15])[N:10]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:9]=2[CH:8]=[C:7]1[C:22]([NH:31][NH2:32])=[O:24]

Participants

Conditions

Temperature: 115 °C

Procedure

A solution of Example 26 (200 mg, 0.49 mmol) in 2-ethoxyethanol (3 ml) was treated with hydrazine hydrate (0.10 ml, 2.04 mmol) and heated at 115° C. overnight. The reaction mixture was concentrated in vacuo. Purification by chromatography (10%-50% EtOAc in DCM, silica) gave the title compound (60 mg, 31%). δH (d3-MeOD) 7.81 (1H, d, J 9.6 Hz), 7.55-7.41 (3H, m), 7.34-7.31 (2H, m), 7.21-7.13 (2H, m), 7.06 (1H, s), 6.99-6.95 (1H, m), 6.42 (1H, d, J 9.6 Hz), 6.17 (1H, s), 5.76 (2H, s). LCMS (ES+) RT 2.78 minutes, 393 [35Cl]:395 [37Cl] 3:1 (M+H+).

Workup

concentrationThe reaction mixture was concentrated in vacuo
customPurification by chromatography (10%-50% EtOAc in DCM, silica)

Sources & evidence

ORD record: ord-f33aef5869b9430e89e9f5712d891a0f
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456286B2

Reaction notes

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