Acetic Acid → HCID 89709223, compound

HRID 1526182Notes

Reaction equation

HRID 1526182 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][CH:37]=1)[O:5][C:6]1[N:7]=[C:8]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:33][CH2:32][C:27]4(OCC[O:28]4)[CH2:26][CH2:25]3)=[C:20]([CH3:34])[CH:19]=2)[C:9]([C:14]([NH2:16])=[O:15])=[N:10][C:11]=1[CH2:12][CH3:13].Cl.C(O)(=O)C.N>O>[NH2:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][CH:37]=1)[O:5][C:6]1[N:7]=[C:8]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:25][CH2:26][C:27](=[O:28])[CH2:32][CH2:33]3)=[C:20]([CH3:34])[CH:19]=2)[C:9]([C:14]([NH2:16])=[O:15])=[N:10][C:11]=1[CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 313Hydrochloric AcidHCID 117667078HCID 117667078, compound

Product 1

HCID 89709223HCID 89709223, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-(3-aminophenoxy)-3-{[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-3-methylphenyl]amino}-6-ethylpyrazine-2-carboxamide (840 mg) and 3 M hydrochloric acid (6 mL) was stirred at 80° C. for 5 hours, and then acetic acid (1.5 mL) was added thereto, followed by stirring at 80° C. overnight. The reaction mixture was left to be cooled, and then water (30 mL) was added thereto, followed by ice-cooling. The pH was adjusted to 9 by the addition of concentrated ammonia. The precipitated solid was collected by filtration and then dried under reduced pressure to obtain 5-(3-aminophenoxy)-6-ethyl-3-{[3-methyl-4-(4-oxopiperidin-1-yl)phenyl]amino}pyrazine-2-carboxamide (0.74 g) as a pale yellow solid.

Workup

  1. stirringby stirring at 80° C. overnight
  2. waitThe reaction mixture was left
  3. temperatureto be cooled
  4. temperaturecooling
  5. filtrationThe precipitated solid was collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-7bcd44a2e8d646bd83c4730c00109a4b
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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