Dimethyl Sulfoxide → HCID 66661963, compound

HRID 969121Notes

Reaction equation

[O:1]=[C:2]1[N:6]([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)[C:5]2[CH:32]=[CH:33][CH:34]=[CH:35][C:4]=2[NH:3]1.[CH3:36]S(C)=O.C(=O)([O-])[O-].[K+].[K+].CI>>[CH3:36][N:3]1[C:4]2[CH:35]=[CH:34][CH:33]=[CH:32][C:5]=2[N:6]([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)[C:2]1=[O:1]

Participants

Reactant 4

HCID 679Dimethyl Sulfoxide

HCID 6328Methyl iodide

HCID 11430Potassium Carbonate

HCID 66661591HCID 66661591, compound

Product 1

HCID 66661963HCID 66661963, compound

Procedure

To a solution of (1R)-1′-({1-[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)phenyl]cyclopropyl}carbonyl)-3H-spiro[furo[3,4-c]pyridine-1,3′-pyrrolidin]-3-one (50 mg, 0.0001 mol) in dimethyl sulfoxide (1 mL, 0.01 mol) were added potassium carbonate (16.3 mg, 0.000118 mol) and methyl iodide (6.67 μL, 0.000107 mol), and the mixture was stirred at room temperature for. 2 hours. The crude product was purified by prep-HPLC. LC/MS: 480.2 (M+H+).

Workup

custom2 hours
customThe crude product was purified by prep-HPLC

Sources & evidence

ORD record: ord-7ba2886e1b754886859a3ed28e231f55
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07304081B2

Reaction notes

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