Tert-butyl 2-chloro-2-cyanoacetate → 3,4-dichloro-N-[1-(5-cyano-4-methoxy-1,3-thiazol-2-yl)piperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide

HRID 2234027Notes

Reaction equation

[NH2:1][C:2]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11]([C:13]2[NH:14][C:15]([CH3:20])=[C:16]([Cl:19])[C:17]=2[Cl:18])=[O:12])[CH2:6][CH2:5]1)=[S:3].Cl[CH:22]([C:30]#[N:31])[C:23]([O:25][C:26](C)(C)C)=O>CO>[Cl:18][C:17]1[C:16]([Cl:19])=[C:15]([CH3:20])[NH:14][C:13]=1[C:11]([NH:10][CH:7]1[CH2:8][CH2:9][N:4]([C:2]2[S:3][C:22]([C:30]#[N:31])=[C:23]([O:25][CH3:26])[N:1]=2)[CH2:5][CH2:6]1)=[O:12]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of N-[1-(aminocarbonothioyl)piperidin-4-yl]-3,4-dichloro-5-methyl-1H-pyrrole-2-carboxamide (Intermediate 95, 0.22 g, 0.7 mmol) and tert-butyl chloro(cyano)acetate (0.12 g, 0.7 mmol) in MeOH was heated to 80° C. in the microwave reactor for 40 minutes. The product precipitated and was filtered off.

Workup

customThe product precipitated
filtrationwas filtered off

Sources & evidence

ORD record: ord-00a0fa6357f8468e89f78b6bf36bd028
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709503B2

Reaction notes

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