Methanol → 4-Mercapto-N-[2-({5-[(2S)-1-methylpyrrolidin-2-yl]pyridin-3-yl}oxy)ethyl]butanamide

HRID 874078Notes

Reaction equation

[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]1[CH:8]=[C:9]([O:13][CH2:14][CH2:15][NH2:16])[CH:10]=[N:11][CH:12]=1.[C:17]1(=[S:22])[O:21][CH2:20][CH2:19][CH2:18]1.CO>O>[SH:22][CH2:17][CH2:18][CH2:19][C:20]([NH:16][CH2:15][CH2:14][O:13][C:9]1[CH:10]=[N:11][CH:12]=[C:7]([C@@H:3]2[CH2:4][CH2:5][CH2:6][N:2]2[CH3:1])[CH:8]=1)=[O:21]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 2-({5-[(2S)-1-methylpyrrolidin-2-yl]pyridin-3-yl}oxy)ethanamine (preparation 12) (1100 mg, 4.971 mmol), in water (10 ml), was treated with γ-thiobutyrolactone (861 ul, 9.94 mmol) and the reaction mixture was heated to 60° C. overnight. It was then evaporated in vacuo to leave a colourless gum, which was pre-adsorbed onto silica from MeOH. This was then chromatographed on a 40 g ISCO column, eluting with EtOAc to EtOAc:MeOH:NH3 80:20:1. The appropriate fractions were evaporated in vacuo to give the title compound as a colourless gum, 690 mg. Yield=43%.

Workup

customIt was then evaporated in vacuo
customto leave a colourless gum, which
customThis was then chromatographed on a 40 g ISCO column
washeluting with EtOAc to EtOAc:MeOH:NH3 80:20:1
customThe appropriate fractions were evaporated in vacuo

Sources & evidence

ORD record: ord-33966f92676040308a5ebc9457734c8d
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980276B2

Reaction notes

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