Hydrochloric Acid → HCID 67115216, compound

HRID 1408539Notes

Reaction equation

HRID 1408539 reaction equation
[Cl:1][C:2]1[CH:27]=[N:26][CH:25]=[C:24]([Cl:28])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[N:9][C:10]([N:13]2[C:17]([CH:18]3[CH2:20][CH2:19]3)=[CH:16][C:15]([CH:21]3[CH2:23][CH2:22]3)=[N:14]2)=[CH:11][CH:12]=1)=[O:5].ClC1C=NC=C(Cl)C=1C(Cl)=O.Cl>C1COCC1.C(OCC)C>[ClH:1].[Cl:28][C:24]1[CH:25]=[N:26][CH:27]=[C:2]([Cl:1])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[N:9][C:10]([N:13]2[C:17]([CH:18]3[CH2:19][CH2:20]3)=[CH:16][C:15]([CH:21]3[CH2:22][CH2:23]3)=[N:14]2)=[CH:11][CH:12]=1)=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 115720223,5-Dichloropyridine-4-carbon chlorideHCID 51353241HCID 51353241, compound

Product 1

HCID 67115216HCID 67115216, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure-2, 3,5-dichloro-N-[6-(3,5-dicyclopropyl-1H-pyrazol-1-yl)pyridin-3-yl]isonicotinamide (24 mg) was prepared from 3,5-dichloroisonicotinoyl chloride (313 mg, 1.5 mmol) and intermediate 30 (200 mg, 0.75 mmol) as a white solid and dissolved in THF. Saturated HCl in diethyl ether was added to this solution at 0° C. and stirred for 15 min Solid that separated out was filtered and dried to give the title compound (7 mg) as a pale-yellow solid. M.P.: 193-195° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 11.34 (s, 1H), 8.82 (s, 2H), 8.69 (d, J 2.4, 1H), 8.24 (dd, J 2.6, 8.9, 1H), 7.78 (d, J 8.9, 1H), 5.83 (s, 1H), 2.72-2.64 (m, 1H), 1.80-1.70 (m, 1H), 0.92-0.82 (m, 4H), 0.70-0.58 (m, 4H). MS (m/z): 413.40 [M−H−HCl]+.

Workup

  1. customthat separated out
  2. filtrationwas filtered
  3. customdried

Sources & evidence

ORD record
ord-34320341d19e4075af6ee5f96747b6de
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

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