Hydrazine hydrate (1:1) → HCID 178487810, compound

HRID 1422964Notes

Reaction equation

O.NN.[CH3:4][O:5][C:6]1[N:7]=[C:8]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][C:14]1[O:13][CH2:12][CH:11]([C@H:20]3[CH2:25][CH2:24][C@H:23]([N:26]4C(=O)C5C(=CC=CC=5)C4=O)[CH2:22][CH2:21]3)[N:10]([CH3:37])[C:9]2=1>C(O)C>[CH3:4][O:5][C:6]1[N:7]=[C:8]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][C:14]1[O:13][CH2:12][CH:11]([C@H:20]3[CH2:25][CH2:24][C@H:23]([NH2:26])[CH2:22][CH2:21]3)[N:10]([CH3:37])[C:9]2=1

Participants

Conditions

Temperature: 50 °C

Procedure

Hydrazine hydrate (2M solution in methanol, 90 μL, 0.18 mmol, 1.0 eq) is added at room temperature to a stirred solution of 2-[trans-4-(6-methoxy-4-methyl-3,4-dihydro-2H-1-oxa-4,5,9-triaza-phenanthren-3-yl)-cyclohexyl]-isoindole-1,3-dione (105 mg, 0.18 mmol, 1.0 eq) in ethanol (3 mL). After 16 hours stirring at 50° C., solvent is removed to afford trans-4-(6-methoxy-4-methyl-3,4-dihydro-2H-1-oxa-4,5,9-triaza-phenanthren-3-yl)-cyclohexylamine as an orange semisolid (80 mg, 93% yield).

Workup

customsolvent is removed

Sources & evidence

ORD record: ord-66066cd5050e4e73b00c4403c4b3d3af
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927541B2

Reaction notes

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