1-Chloro-N,N-2-trimethylpropenylamine → HCID 89832293, compound

HRID 338116Notes

Reaction equation

[C:1]([NH:9][C:10]([NH:12][C:13]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[F:33])[CH:17]([CH2:18]O)[CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]1)=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(N(C)C)=C(C)C>ClCCl>[F:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:13]12[CH2:14][NH:15][CH2:16][CH:17]1[CH2:18][S:11][C:10]([NH:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[N:12]2

Participants

Conditions

Temperature: 0 °C

Procedure

Racemic tert-butyl 3-(benzoylcarbamothioylamino)-3-(2-fluorophenyl)-4-(hydroxymethyl)pyrrolidine-1-carboxylate (2.1 g, 4.39 mmol) is dissolved in dichloromethane (75 mL) and partitioned in equal portions between three reaction vessels. The reaction vessels are cooled to 0° C., and to each vessel is added drop wise 1-chloro-N,N,2-trimethylpropenylamine (2.0 mL, 15 mmol). The reactions are warmed to 22° C., and stirred for 4 hours. The contents of each vessel are passed through a 10 g silica gel plug, washed with methanol (30 ml), and the solvent removed under reduced pressure. The residues are purified by reverse phase HPLC eluting with a gradient of 5 to 100% acetonitrile in 10 mM ammonium bicarbonate solution w/5% methanol (pH 10.0) to give the title compound (3.1 g). ES/MS (m/e): 356 (M+H).

Workup

custompartitioned in equal portions between three reaction vessels
customThe reaction vessels
temperatureThe reactions are warmed to 22° C.
customThe contents of each vessel are passed through a 10 g silica gel plug
washwashed with methanol (30 ml)
customthe solvent removed under reduced pressure
customThe residues are purified by reverse phase HPLC
washeluting with a gradient of 5 to 100% acetonitrile in 10 mM ammonium bicarbonate solution w/5% methanol (pH 10.0)

Sources & evidence

ORD record: ord-c54b29483b3c4296957d57ca59ee85e6
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889856B2

Reaction notes

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