Chlorosuccinimide → HCID 58365133, compound

HRID 60271Notes

Reaction equation

[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:15]3[C:14]4[CH:16]=[C:17]([C:20]#[N:21])[N:18]=[CH:19][C:13]=4[N:12]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:11]=3[N:10]=[CH:9][CH:8]=2)[CH2:3]1.[Cl:30]N1C(=O)CCC1=O>C(#N)C.C(O)(C)C>[Cl:30][C:8]1[CH:9]=[N:10][C:11]2[N:12]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:13]3[CH:19]=[N:18][C:17]([C:20]#[N:21])=[CH:16][C:14]=3[C:15]=2[C:7]=1[N:4]1[CH2:5][CH2:6][C@H:2]([OH:1])[CH2:3]1

Participants

Conditions

Temperature: 35 °C

Procedure

A mixture of (S)-4-(3-hydroxypyrrolidin-1-yl)-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (140 mg, 0.34 mmol) and N-chlorosuccinimide (137 mg, 1.02 mmol) in acetonitrile (1.3 mL) and isopropyl alcohol (0.4 mL) was stirred at 35° C. for 5 hours. The cooled reaction mixture was quenched with saturated aqueous sodium thiosulfate (1 mL), diluted with ethyl acetate (50 mL), and washed with water (20 mL). The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified by flash chromatography (silica, 4 g, ISCO, 0-50% ethyl acetate in heptane) to afford the title compound as a pale yellow solid, which was used in the next step without any further purification (100 mg).

Workup

customThe cooled reaction mixture
customwas quenched with saturated aqueous sodium thiosulfate (1 mL)
additiondiluted with ethyl acetate (50 mL)
washwashed with water (20 mL)
customThe organic layer was separated
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
custompurified by flash chromatography (silica, 4 g, ISCO, 0-50% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-550be6cad23d4367a1130999d7a98953
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440976B2

Reaction notes

Loading…