Formic Acid → HCID 57889619, compound

HRID 1820286Notes

Reaction equation

HRID 1820286 reaction equation
Cl.[NH2:2][C@H:3]([CH:22]([CH3:24])[CH3:23])[C:4]([N:6]1[CH2:11][CH2:10][C@@:9]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)([OH:12])[C:8]([CH3:21])([CH3:20])[CH2:7]1)=[O:5].ClC1N=[C:30]([O:32]C)N=C(OC)N=1.C(O)=O.CN1CCOCC1>CN(C1C=CN=CC=1)C>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([C@@:9]2([OH:12])[CH2:10][CH2:11][N:6]([C:4](=[O:5])[C@H:3]([NH:2][CH:30]=[O:32])[CH:22]([CH3:24])[CH3:23])[CH2:7][C:8]2([CH3:20])[CH3:21])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 67299922HCID 67299922, compound

Product 1

HCID 57889619HCID 57889619, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of (R)-2-amino-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methylbutan-1-one hydrochloride (111 mg, 0.296 mmol), 2-chloro-4,6-dimethoxy-1,3,5-triazine (57.1 mg, 0.325 mmol), formic acid (0.012 mL, 0.325 mmol) and NMM (0.068 mL, 0.62 mmol) CH2Cl2 (10 mL), was added DMAP (3.61 mg, 0.03 mmol). The mixture was stirred at rt for 3 h. The reaction was filtered and the filtrate was washed with Na2CO3, 0.5N HCl, and brine. The organic layer was dried over Na2SO4 and Concentrated to give N—((R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-yl)formamide (76 mg, 0.207 mmol, 70.0% yield).

Workup

  1. filtrationThe reaction was filtered
  2. washthe filtrate was washed with Na2CO3, 0.5N HCl, and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationConcentrated

Sources & evidence

ORD record
ord-731d3c951ec1462ca0e4af13eae51fbb
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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