Acetonitrile → HCID 66662014, compound

HRID 969125Notes

Reaction equation

[NH:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3([C:16]([N:18]4[CH2:22][CH2:21][C@@:20]5([C:30]6[CH:29]=[CH:28][N:27]=[CH:26][C:25]=6[C:24](=[O:31])[O:23]5)[CH2:19]4)=[O:17])[CH2:15][CH2:14]3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C(#N)C.C(N(CC)CC)C.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>>[CH3:42][S:43]([N:1]1[CH2:2][CH:3]=[C:4]([C:7]2[CH:8]=[CH:9][C:10]([C:13]3([C:16]([N:18]4[CH2:22][CH2:21][C@@:20]5([C:30]6[CH:29]=[CH:28][N:27]=[CH:26][C:25]=6[C:24](=[O:31])[O:23]5)[CH2:19]4)=[O:17])[CH2:14][CH2:15]3)=[CH:11][CH:12]=2)[CH2:5][CH2:6]1)(=[O:45])=[O:44]

Participants

Reactant 4

HCID 6342Acetonitrile

HCID 8471Triethylamine

HCID 31297Methanesulfonyl chloride

HCID 66661796HCID 66661796, compound

Product 1

HCID 66662014HCID 66662014, compound

Procedure

To a solution of (1R)-1′-({1-[4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]cyclopropyl}carbonyl)-3H-spiro[furo[3,4-c]pyridine-1,3′-pyrrolidin]-3-one (22 mg, 0.000053 mol) in acetonitrile (0.5 mL, 0.01 mol) were added triethylamine (16.8 μL, 0.000120 mol) and methane sulfonyl chloride. The reaction mixture was stirred at room temperature overnight. The crude product was purified by prep-HPLC. LC/MS: 494.2 (M+H+).

Workup

customThe crude product was purified by prep-HPLC

Sources & evidence

ORD record: ord-bca5caf43817428cb2d69003241961dc
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07304081B2

Reaction notes

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