Hydrazine → HCID 178514340, compound

HRID 1678763Notes

Reaction equation

Cl[C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:6]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][N:19]3[CH2:24][CH2:23][CH:22]([C:25]4[NH:29][C:28]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=5)=[N:27][N:26]=4)[CH2:21][CH2:20]3)=[CH:14][CH:13]=1)=[N:7]2.[NH2:42][NH2:43]>O1CCOCC1>[NH:42]([C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:6]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][N:19]3[CH2:24][CH2:23][CH:22]([C:25]4[NH:29][C:28]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=5)=[N:27][N:26]=4)[CH2:21][CH2:20]3)=[CH:14][CH:13]=1)=[N:7]2)[NH2:43]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 9-2 (5 g, 8.9 mMol) in anhydrous 1,4-dioxane (20 mL) was added hydrazine (5.9 mL, 188.1 mMol). The solution was heated to 100° C. in a microwave reactor for 5 minutes. The solvent was removed in vacuo and was dried azeotropically with toluene three times. The crude solid was triturated with a saturated NaHCO3 solution for 20 minutes. The suspension was filtered and washed with copious amounts of water. The solid was dried azeotropically with toluene three times to yield 9-3 as a tan solid. LC/MS (M+1) calculated: 554.6; observed: 554.2

Workup

customThe solvent was removed in vacuo
dry with materialwas dried azeotropically with toluene three times
customThe crude solid was triturated with a saturated NaHCO3 solution for 20 minutes
filtrationThe suspension was filtered
washwashed with copious amounts of water
dry with materialThe solid was dried azeotropically with toluene three times

Sources & evidence

ORD record: ord-8f08756f0333433ca60b4c3330ce2090
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008317B2

Reaction notes

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