Dimethyl Sulfoxide → HCID 66662224, compound

HRID 557880Notes

Reaction equation

F[C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3([C:17]([N:19]4[CH2:23][CH2:22][C@@:21]5([C:27]6[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=6[C:25](=[O:32])[O:24]5)[CH2:20]4)=[O:18])[CH2:16][CH2:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[NH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1.CS(C)=O>>[N:33]1([C:2]2[N:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][C:11]([C:14]4([C:17]([N:19]5[CH2:23][CH2:22][C@@:21]6([C:27]7[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=7[C:25](=[O:32])[O:24]6)[CH2:20]5)=[O:18])[CH2:16][CH2:15]4)=[CH:10][CH:9]=3)=[CH:4][CH:3]=2)[CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

Reactant 3

HCID 679Dimethyl Sulfoxide

HCID 31268Pyrrolidine

HCID 66661906HCID 66661906, compound

Product 1

HCID 66662224HCID 66662224, compound

Conditions

Temperature: 100 °C

Procedure

A mixture of (1R)-1′-({1-[4-(6-fluoropyridin-3-yl)phenyl]cyclopropyl}carbonyl)-3H-spiro[2-benzofuran-1,3′-pyrrolidin]-3-one (20.0 mg, 0.0000467 mol, example 250), pyrrolidine (7.8 μL, 0.000093 mol) in dimethyl sulfoxide (0.5 mL, 0.007 mol) was heated at 100° C. in a sealed tube for 5 hours. The product was purified by prep-HPLC. LC-MS: 480.2 (M+H+)

Workup

customThe product was purified by prep-HPLC

Sources & evidence

ORD record: ord-799a0d2ab1524cc9962e804530079b80
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058288B2

Reaction notes

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