Hydrochloric Acid → HCID 67048008, compound

HRID 1445289Notes

Reaction equation

HRID 1445289 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, 1H), 8.60 (d, 1H), 8.41 (t, 2H), 8.31 (d, 1H), 7.95 (t, 1H), 7.80 (t, 1H); C12H8N2O.(0.3 H2O).(0.2 ClH). 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-a72c9bbde0d44d7f9b8d9451684ee0dd
Source dataset
uspto-grants-2010_02
Patent number
USRE041150E1

Reaction notes

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