Diisopropylethylamine → HCID 59626733, compound

HRID 2400375Notes

Reaction equation

HRID 2400375 reaction equation
[CH3:1]S(O)(=O)=O.[NH2:6][CH:7]1[C:21](=[O:22])[NH:20][CH2:19][C:10]2[C:11]3[CH:12]=[N:13][NH:14][C:15]=3[C:16]([Cl:18])=[CH:17][C:9]=2[CH2:8]1.C(N([CH:29]([CH3:31])[CH3:30])CC)(C)C.[C:32](=[O:35])(O)[O-:33].[Na+]>C1COCC1.O>[Cl:18][C:16]1[C:15]2[NH:14][N:13]=[CH:12][C:11]=2[C:10]2[CH2:19][NH:20][C:21](=[O:22])[CH:7]([NH:6][C:32](=[O:35])[O:33][C:29]([CH3:31])([CH3:1])[CH3:30])[CH2:8][C:9]=2[CH:17]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 86649246HCID 86649246, compound

Product 1

HCID 59626733HCID 59626733, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 7-amino-4-chloro-6,7,9,10-tetrahydroazepino[3,4-e]indazol-8(3H)-one methanesulfonate from Step C in 1:1 THF/water (100 mL) was added diisopropyl ethylamine (1.1 g, 1.58 mL, 8.65 mmol) and Boc-anhydride (1.88 g, 8.65 mmol) and the reaction allowed to stir at room temperature for 30 minutes. The reaction was poured into a solution of saturated aqueous sodium bicarbonate and the mixture was extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed once with brine (100 mL), dried over anhydrous magnesium sulfate, filtered and concentrated at reduced pressure to give 900 mg of the title compound. MS: m/z=351 (M+1).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×100 mL)
  2. washThe combined organic extracts were washed once with brine (100 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-d8fbffcc70fd4e8ea2be1f8ccccbd378
Source dataset
uspto-grants-2014_08
Patent number
US08796260B2

Reaction notes

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