Diisopropylethylamine → HCID 16734504, compound

HRID 2353580Notes

Reaction equation

HRID 2353580 reaction equation
C[O:2][C:3](=O)[CH:4]=[C:5]([C:25](=[O:44])[NH:26][C:27]1[CH:32]=[C:31]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH:30]=[C:29]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[C:28]=1[O:42][CH3:43])[C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([O:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[CH:8][CH:7]=1.CCN(C(C)C)C(C)C>C1COCC1>[C:33]([C:31]1[CH:32]=[C:27]([N:26]2[C:3](=[O:2])[CH:4]=[C:5]([C:6]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:9]([O:16][CH2:17][CH2:18][N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[CH:8][CH:7]=3)[C:25]2=[O:44])[C:28]([O:42][CH3:43])=[C:29]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[CH:30]=1)([CH3:34])([CH3:35])[CH3:36]

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 67091153HCID 67091153, compound

Product 1

HCID 16734504HCID 16734504, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

In a 40 mL scintillation vial was placed 3-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenylcarbamoyl)-3-[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-acrylic acid methyl ester 51 (25 mg, 0.04 mmol), DIEA (13.6 mL, 0.08 mmol), and 5 mL THF. The reaction was heated to 80° C., stirring for 16 hours. The resulting reaction mixture was concentrated under vacuum and the crude residue purified by reverse phase preparative LC-MS to afford (10.2 mg, 39%) of the desired compound. Calculated mass=607. Observed mass=608.

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated under vacuum
  3. customthe crude residue purified by reverse phase preparative LC-MS

Sources & evidence

ORD record
ord-205b5f7659814b1ca74a0a9d01806691
Source dataset
uspto-grants-2010_07
Patent number
US07749999B2

Reaction notes

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