1,2-Dichloroethane → HCID 57888656, compound

HRID 1820283Notes

Reaction equation

HRID 1820283 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]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 3516526-Aminopyridine-2-carboxylic acidHCID 67299922HCID 67299922, compound

Product 1

HCID 57888656HCID 57888656, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. stirringThe mixture was stirred at rt overnight
  2. customThe reaction was quenched with NaHCO3 (aq)
  3. stirringstirred at rt for 1 h
  4. extractionextracted by EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationAfter concentrating in vacuo
  8. customthe residue was triturated with CH2Cl2
  9. filtrationfiltered

Sources & evidence

ORD record
ord-266fea61655c4a9c9aa639825f541a88
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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