Hydrochloric Acid → HCID 178437676, compound

HRID 869275Notes

Reaction equation

HRID 869275 reaction equation
[C:1]([C:4]1[C:5]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([CH:27]3[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]3)=[C:23]([O:40][CH3:41])[CH:22]=2)=[N:6][C:7]([NH:12][C@H:13]2[CH2:18][CH2:17][C@H:16]([OH:19])[CH2:15][CH2:14]2)=[C:8]([CH2:10][CH3:11])[N:9]=1)(=[O:3])[NH2:2].Cl>C(OCC)(=O)C>[CH2:10]([C:8]1[N:9]=[C:4]([C:1]([NH2:2])=[O:3])[C:5]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([CH:27]3[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]3)=[C:23]([O:40][CH3:41])[CH:22]=2)=[N:6][C:7]=1[NH:12][C@H:13]1[CH2:14][CH2:15][C@H:16]([OH:19])[CH2:17][CH2:18]1)[CH3:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178437678HCID 178437678, compound

Product 1

HCID 178437676HCID 178437676, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of tert-butyl 4-[4-({3-carbamoyl-5-ethyl-6-[(trans-4-hydroxycyclohexyl)amino]pyrazin-2-yl}amino)-2-methoxyphenyl]piperidine-1-carboxylate (Example 382) (270 mg) and ethyl acetate (10 mL), 4M hydrogen chloride in ethyl acetate (4 mL) was added under ice cooling and stirred at room temperature for 1 hour. The reaction liquid was concentrated under reduced pressure, and saturated aqueous sodium hydrogen carbonate and chloroform were added to the residue. The precipitated solid was collected by filtration and dried to give 6-ethyl-5-[(trans-4-hydroxycyclohexyl)amino]-3-[(3-methoxy-4-piperidin-4-ylphenyl)amino]pyrazine-2-carboxamide (85 mg) as a light yellow solid.

Workup

  1. additionwas added under ice cooling
  2. customThe reaction liquid
  3. concentrationwas concentrated under reduced pressure, and saturated aqueous sodium hydrogen carbonate and chloroform
  4. additionwere added to the residue
  5. filtrationThe precipitated solid was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-23c5f6a562694ea2851931545eae6e37
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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