HCID 86677323, compound → N-[4-Methoxy-5-[[4-(1-methyl-1H-indol-3-yl)-2-pyrimidinyl]amino]-2-[methyl[2-(methylamino)ethyl]amino]phenyl]-2-propenamide

HRID 1842668Notes

Reaction equation

HRID 1842668 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH:27][C:28]2[N:33]=[C:32]([C:34]3[C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[N:36]([CH3:43])[CH:35]=3)[CH:31]=[CH:30][N:29]=2)=[CH:5][C:6]([NH:22][C:23](=[O:26])[CH:24]=[CH2:25])=[C:7]([N:9]([CH3:21])[CH2:10][CH2:11][N:12](C)[C:13](=O)OC(C)(C)C)[CH:8]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH3:1][O:2][C:3]1[C:4]([NH:27][C:28]2[N:33]=[C:32]([C:34]3[C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[N:36]([CH3:43])[CH:35]=3)[CH:31]=[CH:30][N:29]=2)=[CH:5][C:6]([NH:22][C:23](=[O:26])[CH:24]=[CH2:25])=[C:7]([N:9]([CH3:21])[CH2:10][CH2:11][NH:12][CH3:13])[CH:8]=1

Participants

4

Reactant 1

HCID 86677323HCID 86677323, compound2×

Product 1

HCID 71496459N-[4-Methoxy-5-[[4-(1-methyl-1H-indol-3-yl)-2-pyrimidinyl]amino]-2-[methyl[2-(methylamino)ethyl]amino]phenyl]-2-propenamideYield 41.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl N-[2-[[5-methoxy-4-[[4-(1-methylindol-3-yl)pyrimidin-2-yl]amino]-2-(prop-2-enoylamino)phenyl]-methylamino]ethyl]-N-methylcarbamate (Intermediate 170, 321 mg, 0.55 mmol) in CH2Cl2 (10 mL) and TFA (2 mL) was stirred at r.t. for 0.5 h and then concentrated in vacuo. The residue was dissolved in 10% CH3OH/CH2Cl2. The resulting solution was washed with sat. NaHCO3, dried (MgSO4) and concentrated in vacuo. Purification by FCC, eluting with 0-20% CH3OH in CH2Cl2 gave the title compound (110 mg, 41%) as a pale yellow solid after trituration with diethyl ether; 1H NMR: 2.35 (3H, s), 2.58-2.62 (2H, m), 2.71 (3H, s), 2.85-2.89 (2H, m), 3.86 (3H, s), 3.92 (3H, s), 5.74 (1H, dd), 6.28 (1H, dd), 6.59 (1H, dd), 6.99 (1H, s), 7.15 (1H, t), 7.21-7.27 (2H, m), 7.53 (1H, d), 7.87 (1H, s), 8.24 (1H, d), 8.32 (1H, d), 8.66 (1H, s), 9.16 (1H, s), 10.33 (1H, s); m/z: ES+ MH+ 486.55.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in 10% CH3OH/CH2Cl2
  3. washThe resulting solution was washed with sat. NaHCO3
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by FCC
  7. washeluting with 0-20% CH3OH in CH2Cl2

Sources & evidence

ORD record
ord-8fa57fff74f945209057a9d2af2c44ed
Source dataset
uspto-grants-2015_02
Patent number
US08946235B2

Reaction notes

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