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Formic Acid → HCID 57889619, compound

HRID 1016216
Notes
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Reaction equation

HRID 1016216 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 14284
4-(Dimethylamino)pyridine
Catalyst

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-e1183691549d4191828eaa76b641d35c
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07985861B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes