Diisopropylethylamine → HCID 86689216, compound

HRID 594954Notes

Reaction equation

HRID 594954 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[C:15]4[CH2:16][NH:17][CH2:18][CH2:19][C:14]=4[NH:13][N:12]=3)=[CH:8][CH:9]=2)[CH:4]=[N:3]1.[N:20]([CH:23]1[CH2:29][CH2:28][CH:27]2[N:30]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:24]1[CH2:25][CH2:26]2)=[C:21]=[O:22].C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[C:15]4[CH2:16][N:17]([C:21]([NH:20][CH:23]5[CH2:29][CH2:28][CH:27]6[N:30]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:24]5[CH2:25][CH2:26]6)=[O:22])[CH2:18][CH2:19][C:14]=4[NH:13][N:12]=3)=[CH:8][CH:9]=2)[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 68066160HCID 68066160, compoundHCID 86689215HCID 86689215, compound

Product 1

HCID 86689216HCID 86689216, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Dimethylformamide (0.7133 mL) was added to a flask containing 3-(1-methyl-1H-indazol-5-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine (54.2 mg, 0.214 mmol) and tert-butyl 2-isocyanato-8-azabicyclo[3.2.1]octane-8-carboxylate (45 mg, 0.178 mmol). Diisopropylethylamine (0.1474 mL, 0.856 mmoL) was added to the flask, and the reaction was allowed to stir at 70° C. for 16 hrs. The reaction was quenched with water and was extracted using ethyl acetate three times. The ethyl acetate layers were combined, dried over sodium sulfate, filtered, and concentrated. The crude was purified using flash chromatography (methanol in dichloromethane 0-20%).

Workup

  1. customThe reaction was quenched with water
  2. extractionwas extracted
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was purified

Sources & evidence

ORD record
ord-1b3f45a1ea934db8a429f71af25d1c11
Source dataset
uspto-grants-2016_01
Patent number
US09242981B2

Reaction notes

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