Pyridine → HCID 178509412, compound

HRID 2402441Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[S:9][C:10]([C:23]3[NH:27][CH:26]=[N:25][N:24]=3)=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[Cl:22])[C:12]=2[C:13]#[N:14])[CH:5]=[CH:4][N:3]=1.N1C=CC=CC=1.[CH:34]1([C:37](Cl)=[O:38])[CH2:36][CH2:35]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:13]([C:12]1[C:11]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[C:10]([C:23]2[NH:27][CH:26]=[N:25][N:24]=2)[S:9][C:8]=1[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:37]([CH:34]2[CH2:36][CH2:35]2)=[O:38])[CH:7]=1)#[N:14]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 2-(2-aminopyridin-4-yl)-4-(2,4-dichlorophenyl)-5-(4H-1,2,4-triazol-3-yl)thiophene-3-carbonitrile (0.100 g, 0.24 mmol) in pyridine (0.39 mL, 4.8 mmol) and methylene chloride (10 mL) was added cyclopropanecarbonyl chloride 0.050 mL, 0.54 mmol) at 0° C. The mixture was stirred at 0° C. for 2 hours. Saturated sodium bicarbonate solution (5 mL) was added and the mixture was vigorously stirred for 15 min. The mixture was extracted with DCM, dried, filtered and evaporated and the residue was purified by column chromatography on silica gel (40 g) using DCM to 3% MeOH in DCM over 30 minutes to afford the product (0.041 g, 36%). LCMS: (FA) ES+, 481, 483. 1H NMR (400 MHz, d4-Methanol) 8.49-8.42 (m, 2H), 8.40 (s, 1H), 7.66 (dd, J=5.58, 1.76 Hz, 1H), 7.62 (t, J=1.16, 1.16 Hz, 1H), 7.46-7.44 (m, 2H), 1.99-1.87 (m, 1H), 1.11-1.03 (m, 2H), 1.00-0.94 (m, 2H)

Workup

stirringthe mixture was vigorously stirred for 15 min
extractionThe mixture was extracted with DCM
customdried
filtrationfiltered
customevaporated
customthe residue was purified by column chromatography on silica gel (40 g)
customover 30 minutes

Sources & evidence

ORD record: ord-78c817b7e2fc45c194760a2be7619da4
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796314B2

Reaction notes

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