2-(Dimethylamino)ethanol → HCID 67313756, compound

HRID 1716410Notes

Reaction equation

HRID 1716410 reaction equation
[C:1]1([CH:7]([NH:9][C:10]([C:12]2[S:13][C:14]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([OH:32])[CH:25]=4)[N:18]=3)=[CH:15][CH:16]=2)=[O:11])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:33][N:34]([CH2:36][CH2:37]O)[CH3:35].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC([N+](C(OC(C)C)=O)=[N-])=O)(C)C>C1COCC1.CS(C)=O>[C:1]1([CH:7]([NH:9][C:10]([C:12]2[S:13][C:14]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH2:37][CH2:36][N:34]([CH3:35])[CH3:33])[CH:25]=4)[N:18]=3)=[CH:15][CH:16]=2)=[O:11])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 22145704Diisopropyl diazodicarboxylateHCID 67314120HCID 67314120, compound

Product 1

HCID 67313756HCID 67313756, compoundYield 1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

5-[2-(3-Hydroxy-4-methoxy-phenylamino)-pyrimidin-4-yl]-thiophene-2-carboxylic acid (1-phenyl-ethyl)-amide (35 mg, 78 μmol), dimethylaminoethanol (26 μL, 156 μmol), and triphenylphosphine (41 mg, 156 μmol) were dissolved in 0.14 mL THF and cooled to 0° C. Diisopropyldiazodicarboxylate (31 μL, 156 μmol) were added dropwise. The reaction mixture was slowly warmed to room temperature and stirred overnight. The crude product was diluted with DMSO and purified by mass triggered reverse phase HPLC to afford 0.3 mg of pure 5-{2-[3-(2-Dimethylamino-ethoxy)-4-methoxy-phenylamino]-pyrimidin-4-yl}-thiophene-2-carboxylic acid (1-phenyl-ethyl)-amide (0.6 μmol, 1%). 1H NMR (500 MHz, DMSO-d6) δ 9.49 (s, 1H), 8.94 (d, J=8 Hz, 1H), 8.47 (d, J=5 Hz, 1H), 7.98 (d, J=4 Hz, 1H), 7.93 (d, J=4 Hz, 1H), 7.57 (m, 1H), 7.38 (m, 2H), 7.31 (m, 4H), 7.23 (m, 1H), 6.88 (d, J=8 Hz, 1H), 5.12 (quintet, J=7.5 Hz, 1H), 4.05 (t, J=6 Hz, 2H), 3.71 (s, 3H), 2.64 (t, J=6 Hz, 2H), 2.17 (s, 6H), 1.48 (d, J=6.5 Hz, 3H). MS: m/z 518 (M+H+).

Workup

  1. temperatureThe reaction mixture was slowly warmed to room temperature
  2. custompurified by mass triggered reverse phase HPLC

Sources & evidence

ORD record
ord-2b52c463da7543dfb1550cb0300c40b0
Source dataset
uspto-grants-2010_09
Patent number
US07803806B2

Reaction notes

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