Triethylamine → HCID 178523576, compound

HRID 880034

Reaction equation

HRID 880034 reaction equation
[OH:1][C:2]1[C:3](=[O:11])[NH:4][CH:5]=[CH:6][C:7]=1[C:8](Cl)=[O:9].[C:12]1([C@@H:18]2[CH2:23][CH2:22][C@H:21]([NH2:24])[CH2:20][CH2:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(CC)CC>C(Cl)Cl>[OH:1][C:2]1[C:3](=[O:11])[NH:4][CH:5]=[CH:6][C:7]=1[C:8]([NH:24][C@H:21]1[CH2:20][CH2:19][C@@H:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:23][CH2:22]1)=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 867300873-Hydroxy-2-oxo-1,2-dihydropyridine-4-carbonyl chloride2×HCID 178418405HCID 178418405, compound2×

Product 1

HCID 178523576HCID 178523576, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-hydroxy-2-oxo-1,2-dihydropyridine-4-carbonyl chloride (Intermediate 17) (38.1 mg, 0.219 mmol) and cis-4-phenylcyclohexanamine (Intermediate 14) (50 mg, 0.29 mmol) in DCM (1 mL) was added Et3N (0.061 mL, 0.44 mmol). The reaction mixture was stirred at rt for 1 h. The reaction mixture was partitioned between H2O and DCM. The DCM layer was dried over Na2SO4 and filtered through a silica gel plug. The solvent was removed under reduced pressure to give Example 36A which was used without further purification.

Workup

  1. customThe reaction mixture was partitioned between H2O and DCM
  2. dry with materialThe DCM layer was dried over Na2SO4
  3. filtrationfiltered through a silica gel plug
  4. customThe solvent was removed under reduced pressure
  5. customto give Example 36A which
  6. customwas used without further purification

Sources & evidence

ORD record
ord-44906a32281c4353b07466489919940a
Source dataset
uspto-grants-2015_03
Patent number
US08993557B2

Linked notes

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