Diisopropylethylamine → HCID 131714815, compound

HRID 364210Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][CH2:12][N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[N:6]=[C:5]3[C:18]4[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][C:19]=4[S:20][C:3]=1[C:4]=23.[Br:26]CC[C:29]1[CH:39]=[CH:38][CH:37]=[C:31]2[C:32]([NH:34][C:35](=[O:36])[C:30]=12)=[O:33].[CH:40](N(CC)C(C)C)(C)[CH3:41]>C(Cl)(Cl)Cl>[BrH:26].[CH2:14]([N:13]([CH2:16][CH3:17])[CH2:12][CH2:11][N:7]1[C:8]2[CH:9]=[CH:10][C:2]([NH:1][CH2:40][CH2:41][N:34]3[C:35](=[O:36])[C:30]4[C:31](=[CH:37][CH:38]=[CH:39][CH:29]=4)[C:32]3=[O:33])=[C:3]3[S:20][C:19]4[CH:21]=[CH:22][C:23]([OH:25])=[CH:24][C:18]=4[C:5]([C:4]=23)=[N:6]1)[CH3:15]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 4.61 g of 5-amino-2-[2-(diethylamino)-ethyl]-2H-benzothiopyrano[4,3,2-cd]indazol-9-ol and 4.3 g of bromoethylphthalimide is heated at 110° C. for 16 hours, then cooled to room tempaerature. The mixture is combined with 300 ml of chloroform and 10 ml of N,N-diisopropylethylamine and heated under reflux for 2 hours, then washed with three 350-ml portions of water. The solution is evaporated to afford an oily solid which is triturated with 2-propanol. The resulting solid is collected and dried to give the title compound, mp 163°-166° C.

Workup

temperaturecooled to room tempaerature
temperatureheated
temperatureunder reflux for 2 hours
washwashed with three 350-ml portions of water
customThe solution is evaporated
customto afford an oily solid which
customis triturated with 2-propanol
customThe resulting solid is collected
customdried

Sources & evidence

ORD record: ord-55a5a1c4881748ba9912d46ef5ed4151
Source dataset: uspto-grants-1986_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04604390

Reaction notes

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