4-(3-Chloro-4-fluoro-phenyl)-6-[4-(3-methyl-5-nitro-pyridin-2-yl)-piperazin-1-yl]-2-(2-methyl-pyrrolidin-1-yl)-pyrimidine → HCID 57761684, compound

HRID 1444115Notes

Reaction equation

HRID 1444115 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[C:13]([N:15]3[CH2:20][CH2:19][N:18]([C:21]4[C:26]([CH3:27])=[CH:25][C:24]([N+:28]([O-])=O)=[CH:23][N:22]=4)[CH2:17][CH2:16]3)[N:12]=[C:11]([N:31]3[CH2:35][CH2:34][CH2:33][CH:32]3[CH3:36])[N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]>CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([N:31]3[CH2:35][CH2:34][CH2:33][CH:32]3[CH3:36])[N:12]=[C:13]([N:15]3[CH2:16][CH2:17][N:18]([C:21]4[N:22]=[CH:23][C:24]([NH2:28])=[CH:25][C:26]=4[CH3:27])[CH2:19][CH2:20]3)[CH:14]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

3

Reactant 1

HCID 114971584-(3-Chloro-4-fluoro-phenyl)-6-[4-(3-methyl-5-nitro-pyridin-2-yl)-piperazin-1-yl]-2-(2-methyl-pyrrolidin-1-yl)-pyrimidine

Product 1

HCID 57761684HCID 57761684, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Heat a mixture of 4-(3-chloro-4-fluoro-phenyl)-6-[4-(3-methyl-5-nitro-pyridin-2-yl)-piperazin-1-yl]-2-(2-methyl-pyrrolidin-1-yl)-pyrimidine (300 mg, 0.59 mmol) and SnCl2-2H2O (529 mg, 2.95 mmol) in EtOAc at 80° C. for 16 h. Cool to room temperature and partition between EtOAc and 1N NaOH. Wash with water, dry the solution (Na2SO4), and concentrate under reduced pressure. Purify the residue by flash column eluting with EtOAc to afford the title compound as a light-yellow solid. 1H NMR (400 MHz, CDCl3): δ 1.30 (t, 3H, J=6.4 Hz, CH3); 1.69 (m, 1H, CH2CH2); 1.91 (m, 1H, CH2CH2); 2.06 (m, 2H, CH2CH2); 2.28 (s, 3H, Ar—CH3); 3.10 (m, 4H); 3.47 (br, 2H, NH2); 3.68 (m, 4H); 3.77 (m, 4H); 4.34 (m, 1H); 6.25 (s, 1H, Ar—H); 6.88 (d, J=2.0 Hz, 1H); 7.18 (m, 1H); 7.70 (d, 1H, J=3.2 Hz); 7.89 (m, 1H); 8.07 (m, 1H).

Workup

  1. temperatureHeat
  2. custompartition between EtOAc and 1N NaOH
  3. washWash with water
  4. dry with materialdry the solution (Na2SO4)
  5. concentrationconcentrate under reduced pressure
  6. customPurify the residue by flash column
  7. washeluting with EtOAc

Sources & evidence

ORD record
ord-3c37064ab005420d9b7443d8b4d07a4d
Source dataset
uspto-grants-2010_02
Patent number
US07662830B2

Reaction notes

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