Isoamyl Nitrite → (1R)-1'-({1-[4-(1,3-Thiazol-4-yl)phenyl]cyclopropyl}carbonyl)-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one

HRID 2275568Notes

Reaction equation

N(OCCC(C)C)=O.N[C:10]1[S:11][CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3([C:24]([N:26]4[CH2:30][CH2:29][C@@:28]5([C:34]6[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=6[C:32](=[O:39])[O:31]5)[CH2:27]4)=[O:25])[CH2:23][CH2:22]3)=[CH:17][CH:16]=2)[N:14]=1>O1CCOCC1>[S:11]1[CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3([C:24]([N:26]4[CH2:30][CH2:29][C@@:28]5([C:34]6[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=6[C:32](=[O:39])[O:31]5)[CH2:27]4)=[O:25])[CH2:23][CH2:22]3)=[CH:17][CH:16]=2)[N:14]=[CH:10]1

Participants

Conditions

Temperature: 80 °C

Procedure

Isoamyl nitrite (10.0 μL) was added to a solution of (1R)-1′-({1-[4-(2-amino-1,3-thiazol-4-yl)phenyl]cyclopropyl}carbonyl)-3H-spiro[2-benzofuran-1,3′-pyrrolidin]-3-one (25.0 mg, 0.06 mmol) in 1,4-dioxane (1.0 mL), and the reaction mixture was stirred at 80° C. for 2 hours. Then the solvent from the mixture was removed and the crude product was purified by prep-HPLC. LC-MS: 417.1 (M+H)+.

Workup

customThen the solvent from the mixture was removed
customthe crude product was purified by prep-HPLC

Sources & evidence

ORD record: ord-5f9ca4f8762d403597bae2e2f7142843
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126927B2

Reaction notes

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