Acetic Acid → HCID 86345770, compound

HRID 1772683Notes

Reaction equation

HRID 1772683 reaction equation
C(OP([CH2:9][C:10]1[CH:19]=[C:18]([C:20]([O:22]CC)=[O:21])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1)(OCC)=O)C.CN(C=O)C.[H-].[Na+].[O:32]1[CH2:37][CH2:36][N:35]([C:38]2[C:39]3[N:40]([CH:44]=[C:45]([CH:47]=O)[N:46]=3)[CH:41]=[CH:42][N:43]=2)[CH2:34][CH2:33]1.CC(O)=O.Cl>C1COCC1>[O:32]1[CH2:33][CH2:34][N:35]([C:38]2[C:39]3[N:40]([CH:44]=[C:45](/[CH:47]=[CH:9]/[C:10]4[CH:19]=[C:18]([C:20]([OH:22])=[O:21])[C:17]5[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=5)[N:11]=4)[N:46]=3)[CH:41]=[CH:42][N:43]=2)[CH2:36][CH2:37]1

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 846955128-(4-Morpholinyl)imidazo[1,2-a]pyrazine-2-carboxaldehydeHCID 117728170HCID 117728170, compound

Product 1

HCID 86345770HCID 86345770, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound 45a (124 mg, 0.353 mmol) in DMF (3.5 mmol) was treated with 60% NaH (42.3 mg, 1.05 mmol) at 0° C. The resulting mixture was stirred at rt for 15 min, cooled to 0° C. and treated with compound 45b (90.2 mmol, 0.388 mmol) in THF (2 mL). The resulting mixture was stirred for 30 min, cooled in a dry ice/acetone bath and treated with HOAc (0.060 mL, 1.05 mmol). The reaction mixture was then allowed to warm to rt and the pH was adjusted to about 5 with concentrated HCl. The precipitate formed was collected by filtration and dried under reduced pressure to obtain (E)-2-(2-(8-morpholinoimidazo[1,2-a]pyrazin-2-yl)vinyl)quinoline-4-carboxylic acid.

Workup

  1. temperaturecooled to 0° C.
  2. stirringThe resulting mixture was stirred for 30 min
  3. temperaturecooled in a dry ice/acetone bath
  4. temperatureto warm to rt
  5. customThe precipitate formed
  6. filtrationwas collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-e8f015bc5e474831824a9e81c46b7d7f
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

Loading…