(Diethylamino)sulfur trifluoride → HCID 90333503, compound

HRID 595773Notes

Reaction equation

[F:1][C:2]1[C:3]2[CH:4]=[C:5]3[C:14]4[N:13]=[C:12]([C:15]5[C:16]([N:35]([CH3:40])[S:36]([CH3:39])(=[O:38])=[O:37])=[CH:17][C:18]6[O:22][C:21]([C:23]7[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=7)=[C:20]([C:30]([NH:32][CH3:33])=[O:31])[C:19]=6[CH:34]=5)[CH:11]=[CH:10][C:9]=4[CH2:8][CH:7]([CH2:41]O)[N:6]3[C:43]=2[CH:44]=[CH:45][CH:46]=1.CCN(S(F)(F)[F:53])CC>C(Cl)Cl.C(OCC)(=O)C>[F:1][C:2]1[C:3]2[CH:4]=[C:5]3[C:14]4[N:13]=[C:12]([C:15]5[C:16]([N:35]([CH3:40])[S:36]([CH3:39])(=[O:37])=[O:38])=[CH:17][C:18]6[O:22][C:21]([C:23]7[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=7)=[C:20]([C:30]([NH:32][CH3:33])=[O:31])[C:19]=6[CH:34]=5)[CH:11]=[CH:10][C:9]=4[CH2:8][CH:7]([CH2:41][F:53])[N:6]3[C:43]=2[CH:44]=[CH:45][CH:46]=1

Participants

Conditions

Temperature: 0 °C

Procedure

5-(11-fluoro-6-(hydroxymethyl)-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (40 mg, 0.062 mmol) was dissolved in DCM (2 ml) and cooled to 0° C., followed by addition of DAST (0.025 ml, 0.187 mmol). The mixture was stirred at 0° C. for 1 h, then at RT for 30 min and then concentrated in vacuo. Preparative TLC (50% DCM in ethyl acetate) gave 5-(11-fluoro-6-(fluoromethyl)-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (14 mg, yield: 35%). MS (M+H)+: 645.

Workup

waitat RT for 30 min
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-6070dcf5b1c94bd3b4e458aba2c0ab0d
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09243002B2

Reaction notes

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