α-Methyl-4-(1H-pyrrol-1-yl)benzenemethanamine → HCID 86730227, compound

HRID 1850194Notes

Reaction equation

HRID 1850194 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[C@@H:12]([CH:13]([CH3:15])[CH3:14])[CH2:11][O:10][C:9]2=[O:16])[CH:5]=[CH:4][N:3]=1.[N:17]1([C:22]2[CH:27]=[CH:26][C:25]([CH:28]([NH2:30])[CH3:29])=[CH:24][CH:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18]1>CS(C)=O.CCOC(C)=O>[N:17]1([C:22]2[CH:27]=[CH:26][C:25]([C@H:28]([NH:30][C:2]3[N:7]=[C:6]([N:8]4[C@@H:12]([CH:13]([CH3:15])[CH3:14])[CH2:11][O:10][C:9]4=[O:16])[CH:5]=[CH:4][N:3]=3)[CH3:29])=[CH:24][CH:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18]1.[N:17]1([C:22]2[CH:27]=[CH:26][C:25]([C@@H:28]([NH:30][C:2]3[N:7]=[C:6]([N:8]4[C@@H:12]([CH:13]([CH3:15])[CH3:14])[CH2:11][O:10][C:9]4=[O:16])[CH:5]=[CH:4][N:3]=3)[CH3:29])=[CH:24][CH:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18]1

Participants

6

Reactant 2

HCID 16394844α-Methyl-4-(1H-pyrrol-1-yl)benzenemethanamineHCID 86730167(S)-3-(2-chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-one

Product 2

HCID 86730227HCID 86730227, compoundHCID 86730228HCID 86730228, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)-3-(2-chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-one (44 mg, 0.18 mmol) and 1-(4-(1H-pyrrol-1-yl)phenyl)ethanamine (33.9 mg, 0.182 mmol, 1 equiv) in DMSO (1 mL) was heated at 110° C. for 2 h. The reaction mixture was diluted with EtOAc (8 mL) and washed with water (30 mL). After separation, the aqueous phase was extracted with EtOAc (3×8 mL). Combined organics were dried over Na2SO4, filtered and concentrated. Silica gel column chromatography (EtOAc/Heptane 10 to 50%) provided (S)-3-(2-((R)-1-(4-(1H-pyrrol-1-yl)phenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one and (S)-3-(2-((S)-1-(4-(1H-pyrrol-1-yl)phenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one.

Workup

  1. washwashed with water (30 mL)
  2. customAfter separation
  3. extractionthe aqueous phase was extracted with EtOAc (3×8 mL)
  4. dry with materialCombined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-82425b5d34d946e9b914a59bcaa6658a
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

Loading…