Acetic Acid → 3,4-Dichloro-5-methyl-N-(1-nitrosopiperidin-4-yl)-1H-pyrrole-2-carboxamide

HRID 2233874Notes

Reaction equation

[N:1]([O-:3])=O.[Na+].FC(F)(F)C([O-])=O.[Cl:12][C:13]1[C:17]([Cl:18])=[C:16]([CH3:19])[NH:15][C:14]=1[C:20]([NH:22][CH:23]1[CH2:28][CH2:27][NH2+:26][CH2:25][CH2:24]1)=[O:21].C(O)(=O)C>O.C(O)C.O>[Cl:12][C:13]1[C:17]([Cl:18])=[C:16]([CH3:19])[NH:15][C:14]=1[C:20]([NH:22][CH:23]1[CH2:28][CH2:27][N:26]([N:1]=[O:3])[CH2:25][CH2:24]1)=[O:21]

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of NaNO2 (1.7 g, 24.6 mmol) in 20 ml of water was added to a solution of 4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidinium trifluoroacetate (Intermediate 86; 4 g, 10.3 mmol) and 400 μl acetic acid in 60 ml of 1:1 EtOH—H2O. The mixture was heated to 90° C. for 1 hour. After cooling to room temperature, 200 ml of water was added. White solids were collected by filtration and dried in vacuo (2.8 g).

Workup

temperatureAfter cooling to room temperature
filtrationWhite solids were collected by filtration
customdried in vacuo (2.8 g)

Sources & evidence

ORD record: ord-df58e45c1d7c497faec733b0e8249d0d
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709503B2

Reaction notes

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