Dimethylamine → HCID 23144688, compound

HRID 337498Notes

Reaction equation

Cl[CH2:2][C:3]1[CH:29]=[CH:28][C:6]([C:7]([NH:9][C:10]2[S:11][C:12]([C:20]([CH:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[O:21])=[C:13]([C:15]3[O:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)=[O:8])=[CH:5][CH:4]=1.[CH3:30][NH:31][CH3:32].C1COCC1>>[CH3:30][N:31]([CH2:2][C:3]1[CH:29]=[CH:28][C:6]([C:7]([NH:9][C:10]2[S:11][C:12]([C:20]([CH:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[O:21])=[C:13]([C:15]3[O:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)=[O:8])=[CH:5][CH:4]=1)[CH3:32]

Participants

Reactant 3

HCID 674Dimethylamine

HCID 8028Tetrahydrofuran

HCID 23144430HCID 23144430, compound

Product 1

HCID 23144688HCID 23144688, compoundYield 44%

Conditions

Temperature: 60 °C

Procedure

Compound 478 (340 mg, 0.789 mmol) was added to a 2 mol/L solution of dimethylamine in THF (10 mL, 39.5 mmol), followed by stirring overnight at 60° C. The solvent was distilled away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (chloroform:methanol=19:1), followed by reslurrying with a mixed solvent of ethanol and diethyl ether to afford the entitled Compound 479 (153 mg, 44%) as a yellow solid.

Workup

distillationThe solvent was distilled away under reduced pressure
customthe resulting residue was purified through silica gel column chromatography (chloroform:methanol=19:1)

Sources & evidence

ORD record: ord-7b5361dde0744dbc96f39892ac3dec42
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889718B2

Reaction notes

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