2-(Dimethylamino)ethanol → HCID 59375035, compound

HRID 662000Notes

Reaction equation

[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[C:21]2[C:20]3[C:15](=[CH:16][C:17]([C:22]([N:24]4[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]4)=[O:23])=[CH:18][CH:19]=3)[NH:14][C:13]=2[C:12]([C:31]([NH2:33])=[O:32])=[CH:11][CH:10]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[CH3:65][N:66]([CH3:70])[CH2:67][CH2:68]O>O1CCOCC1.C1COCC1>[CH3:65][N:66]([CH3:70])[CH2:67][CH2:68][O:8][C:7]1[C:2]([F:1])=[C:3]([C:9]2[C:21]3[C:20]4[C:15](=[CH:16][C:17]([C:22]([N:24]5[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]5)=[O:23])=[CH:18][CH:19]=4)[NH:14][C:13]=3[C:12]([C:31]([NH2:33])=[O:32])=[CH:11][CH:10]=2)[CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of 4-(2-fluoro-3-hydroxyphenyl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide (Intermediate 84-1, 20 mg, 0.045 mmol) and polymer-supported triphenylphosphine (2.63 mmol/g, 0.358 mmol) in 1,4-dioxane was treated at 0° C. with a solution of diethyl azodicarboxylate (19.5 mg, 0.157 mmol) in THF (0.5 mL), followed after 5 min by a solution of 2-(dimethylamino)ethanol (10 mg, 0.112 mmol) in THF (0.5 mL). The mixture was heated in a sealed tube by microwave irradiation at 90-100° C. for 30 min. The resulting mixture was filtered, the solids were washed with methanol, and the filtrates were concentrated and purified by preparative HPLC to provide 4-(3-(2-(dimethylamino)ethoxy)-2-fluorophenyl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide. Mass spectrum m/z 518.2 (M+H)+.

Workup

filtrationThe resulting mixture was filtered
washthe solids were washed with methanol
concentrationthe filtrates were concentrated
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-e923903a3c2b472bab2b7e1868fd3718
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084620B2

Reaction notes

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