2-Methylpyrrolidine → HCID 57761162, compound

HRID 230964Notes

Reaction equation

HRID 230964 reaction equation
C(S([C:11]1[N:16]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([Cl:24])[CH:18]=2)[CH:14]=[C:13]([N:25]2[CH2:30][CH2:29][N:28]([C:31]3[C:36]([Cl:37])=[CH:35][CH:34]=[CH:33][N:32]=3)[CH2:27][C@H:26]2[CH3:38])[N:12]=1)(=O)=O)C1C=CC=CC=1.[CH3:39][CH:40]1[CH2:44][CH2:43][CH2:42][NH:41]1>O1CCOCC1>[Cl:24][C:19]1[CH:18]=[C:17]([C:15]2[CH:14]=[C:13]([N:25]3[CH2:30][CH2:29][N:28]([C:31]4[C:36]([Cl:37])=[CH:35][CH:34]=[CH:33][N:32]=4)[CH2:27][C@H:26]3[CH3:38])[N:12]=[C:11]([N:41]3[CH2:42][CH2:43][CH2:44][CH:40]3[CH3:39])[N:16]=2)[CH:22]=[CH:21][C:20]=1[F:23]

Participants

4

Reactant 2

HCID 130032-MethylpyrrolidineHCID 57761127HCID 57761127, compound

Product 1

HCID 57761162HCID 57761162, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Dissolve 2-(benzylsulfonyl)-4-(3-chloro-4-fluorophenyl)-6-((R)-4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl)pyrimidine (57 mg, 0.1 mmol) and 2-methylpyrrolidine (0.5 mmol) in dioxane (1.0 mL) under nitrogen atmosphere and beat at 110° C. for 72 hours. Concentrate under vacuum to afford crude product and purify by flash column chromatography using 5% EtOAc/hexane to afford the title product as white amorphous solid. NMR (CDCl3) δ 1.31 (3H, d, J=1.5), 1.41 (3H, dd), 1.69 (1H, m), 1.9 (1H, m), 2.0 (2H, m), 2.98 (2H, m), 3.39 (1H, m), 3.65 (2H, m), 3.82 (2H, m), 4.35 (2H, m), 4.68 (1H, m), 6.22 (1H, s), 6.86 (1H, m), 7.16 (1H, t), 7.61 (1H, d, J=1.6), 7.88 (1H, m), 8.07 (1H, m), 8.20 (1H, m). Mass spec m/z=501.13.

Workup

  1. concentrationConcentrate under vacuum
  2. customto afford crude product
  3. custompurify by flash column chromatography

Sources & evidence

ORD record
ord-566f21af39df40fe9df94d26e370628e
Source dataset
uspto-grants-2009_07
Patent number
US07566712B2

Reaction notes

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