Methanol → HCID 178425783, compound

HRID 931186Notes

Reaction equation

HRID 931186 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][C:9](N2C(C)=CC=CC2=O)=O)=[CH:6][CH:5]=[C:4]([N:19]2[CH2:24][CH2:23][CH2:22][C@@H:21]([C:25]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[O:26])[CH2:20]2)[N:3]=1.CO.[CH2:34]([OH:38])[CH:35](C)[CH3:36].C[O-].[Na+]>O>[CH3:2][C:7]1[N:8]([CH2:9][C:9]2[NH:1][C:2]3=[N:3][C:4]([N:19]4[CH2:24][CH2:23][CH2:22][C@@H:21]([C:25]([N:27]5[CH2:28][CH2:29][CH2:30][CH2:31]5)=[O:26])[CH2:20]4)=[CH:5][CH:6]=[C:7]3[N:8]=2)[C:34](=[O:38])[CH:35]=[CH:36][CH:6]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6560IsobutanolHCID 10942334Sodium MethoxideHCID 117966360(R)-N-(2-amino-6-(3-(pyrrolidine-1-carbonyl)piperidin-1-yl)pyridin-3-yl)-6-methyl-2-oxopyridine-1(2H)-carboxamide

Product 1

HCID 178425783HCID 178425783, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

Into a vial were added (R)—N-(2-amino-6-(3-(pyrrolidine-1-carbonyl)piperidin-1-yl)pyridin-3-yl)-6-methyl-2-oxopyridine-1(2H)-carboxamide (1 equiv) and a solution of methanol and isobutanol (1:1, 1.5 mL). Sodium methoxide (2.0 equiv) was added and the reaction mixture was shaken at 110° C. for 2 h. Water was added and the mixture was extracted with a mixture of methanol/dichloromethane (1:1). The organics were concentrated by Speedvac and the crude material was purified via preparative HPLC to afford the title compound. MS (ES+) (M+H) 421.4; UPLC 1.09 min (Method T).

Workup

  1. extractionthe mixture was extracted with a mixture of methanol/dichloromethane (1:1)
  2. concentrationThe organics were concentrated by Speedvac
  3. customthe crude material was purified via preparative HPLC

Sources & evidence

ORD record
ord-3b209e8334184882b3fa136a3d3cf5f9
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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