Diisopropylethylamine → HCID 59333961, compound

HRID 331082Notes

Reaction equation

HRID 331082 reaction equation
Cl.[CH2:2]([O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]2[C:13]3[CH2:19][NH:18][C:17]([CH3:21])([CH3:20])[C:14]=3[NH:15][N:16]=2)[N:6]=1)[CH3:3].C(N(C(C)C)CC)(C)C.[Cl:31][C:32](Cl)([O:34]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH2:2]([O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]2[C:13]3[CH2:19][N:18]([C:32]([Cl:31])=[O:34])[C:17]([CH3:20])([CH3:21])[C:14]=3[NH:15][N:16]=2)[N:6]=1)[CH3:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 68595581HCID 68595581, compound

Product 1

HCID 59333961HCID 59333961, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
22 °C

Procedure

To a −78° C. solution of N-(4-ethoxypyrimidin-2-yl)-6,6-dimethyl-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-3-amine hydrochloride (0.300 g, 1.09 mmol) in CH2Cl2 (15 mL) and diisopropylethylamine (0.952 mL, 5.47 mmol) was added triphosgene (0.227 g, 0.766 mmol) in CH2Cl2 (5 mL) dropwise over 10 min. The reaction was quenched with H2O (10 mL), warmed to 22° C., and made pH 8-9 with NaHCO3. The aqueous layer was extracted with CH2Cl2 (2×30 mL) and the combined organic layers washed with brine (1×30 mL), dried over MgSO4, and concentrated to give the desired product M1(i) as a brown solid (0.35 g, 95%). Mass Spectrum: Calcd for C14H18ClN6O2 (M+H): 337. Found: 337.

Workup

  1. customThe reaction was quenched with H2O (10 mL)
  2. extractionThe aqueous layer was extracted with CH2Cl2 (2×30 mL)
  3. washthe combined organic layers washed with brine (1×30 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-167b2c32fc264364a31189a8859c1369
Source dataset
uspto-grants-2014_11
Patent number
US08877761B2

Reaction notes

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