Diisopropylethylamine → HCID 57761684, compound

HRID 2195048Notes

Reaction equation

HRID 2195048 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([Cl:15])[CH:9]=2)[N:5]=[C:4]([N:16]2[CH2:20][CH2:19][CH2:18][CH:17]2[CH3:21])[N:3]=1.[CH3:22][C:23]1[C:24]([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)=[N:25][CH:26]=[C:27]([N+:29]([O-])=O)[CH:28]=1.CCN(C(C)C)C(C)C>CC(N(C)C)=O>[Cl:15][C:10]1[CH:9]=[C:8]([C:6]2[N:5]=[C:4]([N:16]3[CH2:20][CH2:19][CH2:18][CH:17]3[CH3:21])[N:3]=[C:2]([N:35]3[CH2:36][CH2:37][N:32]([C:24]4[N:25]=[CH:26][C:27]([NH2:29])=[CH:28][C:23]=4[CH3:22])[CH2:33][CH2:34]3)[CH:7]=2)[CH:13]=[CH:12][C:11]=1[F:14]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 566870601-(3-Methyl-5-nitropyridin-2-yl)piperazineHCID 866495774-Chloro-6-(3-chloro-4-fluoro-phenyl)-2-(2-methyl-pyrrolidin-1-yl)-pyrimidine

Product 1

HCID 57761684HCID 57761684, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Heat a mixture of 4-chloro-6-(3-chloro-4-fluoro-phenyl)-2-(2-methyl-pyrrolidin-1-yl)-pyrimidine (210 mg), 1-(3-Methyl-5-nitro-pyridin-2-yl)-piperazine, and DIEA (185 mg, 1.44 mmol) in DMA at 120° 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-0e88010ab4534496addd5f6a05e604b8
Source dataset
uspto-grants-2012_12
Patent number
US08334382B2

Reaction notes

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