Pivaloyl chloride → HCID 178482411, compound

HRID 472104Notes

Reaction equation

HRID 472104 reaction equation
[CH3:1][N:2]([C:20]1[C:21]2[CH:28]=[CH:27][NH:26][C:22]=2[N:23]=[CH:24][N:25]=1)[C@H:3]1[CH2:8][CH2:7][C@H:6]([CH2:9][S:10]([N:13]2[CH2:18][CH2:17][CH2:16][C@@H:15]([OH:19])[CH2:14]2)(=[O:12])=[O:11])[CH2:5][CH2:4]1.CCN(C(C)C)C(C)C.[C:38](Cl)(=[O:43])[C:39]([CH3:42])([CH3:41])[CH3:40]>CN(C=O)C>[C:38]([O:19][C@@H:15]1[CH2:16][CH2:17][CH2:18][N:13]([S:10]([CH2:9][C@H:6]2[CH2:5][CH2:4][C@H:3]([N:2]([CH3:1])[C:20]3[C:21]4[CH:28]=[CH:27][NH:26][C:22]=4[N:23]=[CH:24][N:25]=3)[CH2:8][CH2:7]2)(=[O:12])=[O:11])[CH2:14]1)(=[O:43])[C:39]([CH3:42])([CH3:41])[CH3:40]

Participants

5

Reactant 3

HCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 178482410HCID 178482410, compound

Product 1

HCID 178482411HCID 178482411, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of trans-(R)-1-((4-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)methylsulfonyl)piperidin-3-ol (0.400 g, 0.98 mmol), DMF (10 mL), and DIEA (0.25 mL, 1.4 mmol) was treated with pivaloyl chloride (0.10 mL, 0.81 mmol) and the mixture stirred at ambient temperature overnight. The mixture was concentrated and the resulting residue chromatographed over SiO2 using 0→5% MeOH in CH2Cl2. The desired product fractions were pooled and concentrated to afford the title compound (0.182 g, 38%). MS for C24H37N5O4S (ESI) (MH)+ m/z=492.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe resulting residue chromatographed over SiO2 using 0→5% MeOH in CH2Cl2
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ab53547d02be44afa6ac91a2ca123716
Source dataset
uspto-grants-2014_01
Patent number
US08633206B2

Reaction notes

Loading…