Diisopropylethylamine → HCID 66739040, compound

HRID 1465050Notes

Reaction equation

HRID 1465050 reaction equation
[NH2:1][C:2]1[C:3]2[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:12]([CH3:23])([CH3:22])[C:4]=2[N:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.CCN(C(C)C)C(C)C.Cl.[N:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[C:40](Cl)=[O:41]>C(Cl)Cl>[CH3:23][C:12]1([CH3:22])[C:4]2[N:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=[C:2]([NH:1][C:40](=[O:41])[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][N:34]=3)[C:3]=2[CH2:14][N:13]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 135033Picolinoyl Chloride HydrochlorideHCID 573530855-tert-Butyl 1-ethyl 3-amino-6,6-dimethyl-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate

Product 1

HCID 66739040HCID 66739040, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-tert-butyl 1-ethyl 3-amino-6,6-dimethyl-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate, A1(I), (7.32 g, 22.56 mmol) and DIPEA (12 mL) in CH2Cl2 (60 mL), picolinoyl chloride hydrochloride, A1(II), (4.82 g, 27.07 mmol) was added slowly. The reaction was stirred at room temperature for 2 hrs. The reaction mixture was diluted with CH2Cl2 (50 mL), washed with water (2×30 mL), sat. NaCl (brine), and dried over MgSO4, filtered and concentrated to give A1(III) (9.12 g, 94% yield). 1H NMR (400 MHz, CDCl3-d) δ ppm 1.39-1.50 (m, 2H) 1.49-1.58 (m, 10H) 1.72 (s, 3H) 1.78 (s, 3H) 4.63 (q, J=7.07 Hz, 2H) 4.81 (d, J=19.45 Hz, 2H) 7.46-7.58 (m, 1H) 7.82-7.97 (m, 1H) 8.25 (dd, J=7.71, 3.41 Hz, 1H) 8.73 (dd, J=9.60, 4.55 Hz, 1H).

Workup

  1. washwashed with water (2×30 mL), sat. NaCl (brine)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give A1(III) (9.12 g, 94% yield)

Sources & evidence

ORD record
ord-e48f6289871f4caeb62ff3e566e8e504
Source dataset
uspto-grants-2015_04
Patent number
US08999981B2

Reaction notes

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