Hydrochloric Acid → HCID 67048008, compound

HRID 1767684Notes

Reaction equation

HRID 1767684 reaction equation
CC(C)(C)C(N[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:11]=1[C:12]1[CH:26]=[CH:25][CH:24]=[CH:23][C:13]=1[C:14]([N:16](C(C)C)C(C)C)=O)=O.Cl.C[OH:31]>>[C:10]1(=[O:31])[C:11]2[C:6](=[N:16][CH:14]=[C:13]3[C:12]=2[CH:26]=[CH:25][CH:24]=[CH:23]3)[CH:7]=[N:8][CH2:9]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11003443HCID 11003443, compound

Product 1

HCID 67048008HCID 67048008, compound

Procedure

All of 2-[3-(2,2-dimethyl-propionylamino)-pyridin-4-yl]-N,N-diisopropylbenzamide from the previous step was carried on and dissolved in methanol (20 mL). Concentrated HCl (1 mL) was added, followed by 24 h of refluxing. A white solid which precipitated out of solution was filtered and dissolved in H2O. After 15 minutes of stirring, the free base crashed out of solution. The solid was filtered and dried, providing 150 mg (33% for two steps) of the desired final product as a white solid. Mp=303–309° C.; 1H NMR (DMSO-d6, 300 MHz) δ 8.70 (s, 1 H), 8.60 (d, 1 H), 8.41 (t, 2 H), 8.31 (d, 1 H), 7.95 (t, 1 H), 7.80 (t, 1 H); C12H8N2O.(0.3H2O).(0.2ClH). Anal: Calcd for: C, 68.99; H, 4.25; N, 13.41. Found: C, 68.83; H, 3.99; N, 13.26.

Workup

  1. temperatureof refluxing
  2. customA white solid which precipitated out of solution
  3. filtrationwas filtered
  4. dissolutiondissolved in H2O
  5. filtrationThe solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-ecfb9e9b5e344bc5b2397cb184cf44a7
Source dataset
uspto-grants-2007_06
Patent number
US07235557B2

Reaction notes

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