1,2-Dichloroethane → HCID 57888656, compound
Reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.[NH2:35][C@H:36]([CH:55]([CH3:57])[CH3:56])[C:37]([N:39]1[CH2:44][CH2:43][C@@:42]([C:46]2[CH:51]=[CH:50][C:49]([Cl:52])=[CH:48][CH:47]=2)([OH:45])[C:41]([CH3:54])([CH3:53])[CH2:40]1)=[O:38]>CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([NH:35][C@H:36]([CH:55]([CH3:57])[CH3:56])[C:37]([N:39]2[CH2:44][CH2:43][C@@:42]([C:46]3[CH:47]=[CH:48][C:49]([Cl:52])=[CH:50][CH:51]=3)([OH:45])[C:41]([CH3:53])([CH3:54])[CH2:40]2)=[O:38])=[O:10])[CH:5]=[CH:4][CH:3]=1Participants
Procedure
To a suspension of 6-aminopicolinic acid (33 mg, 0.24 mmol) in DMF (2 mL) was added EDC (45.9 mg, 0.24 mmol), HOBt (32.3 mg, 0.24 mmol). The mixture was stirred at rt for 0.5 h, then was added DIPEA (0.083 mL, 0.48 mmol) and (R)-2-amino-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methylbutan-1-one hydrochloride (90 mg, 0.239 mmol). The mixture was stirred at rt overnight. The reaction was quenched with NaHCO3 (aq) and stirred at rt for 1 h, extracted by EtOAc, washed with brine and dried over Na2SO4. After concentrating in vacuo, the residue was triturated with CH2Cl2 and filtered to give a yellow solid as 6-amino-N—((R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-yl)picolinamide (86 mg, 0.187 mmol, 78% yield).
Workup
- stirringThe mixture was stirred at rt overnight
- customThe reaction was quenched with NaHCO3 (aq)
- stirringstirred at rt for 1 h
- extractionextracted by EtOAc
- washwashed with brine
- dry with materialdried over Na2SO4
- concentrationAfter concentrating in vacuo
- customthe residue was triturated with CH2Cl2
- filtrationfiltered
Sources & evidence
- ORD record
- ord-4a2332be09c941388179e2b6b9c3e774
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07985861B2
Reaction notes
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