Diisopropylethylamine → HCID 90010998, compound

HRID 929890Notes

Reaction equation

HRID 929890 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]2[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=2)[CH2:2]1.C(N(C(C)C)CC)(C)C.[N:20]([C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1)=[C:21]=[O:22]>ClCCl>[N:7]1[CH:8]=[CH:9][CH:10]=[C:5]([CH:3]2[CH2:4][N:1]([C:21]([NH:20][C:23]3[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=3)=[O:22])[CH2:2]2)[CH:6]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 28045423138-53-6HCID 203961083-(Azetidin-3-yl)pyridine

Product 1

HCID 90010998HCID 90010998, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 20 mL vial was added 3-(azetidin-3-yl)pyridine, bistrifluoroacetic acid (75 mg, 0.207 mmol) and diisopropylethylamine (0.109 ml, 0.622 mmol) in dichloromethane (2072 μl. Methyl 4-isocyanatobenzoate (47.7 mg, 0.269 mmol) was added, and the mixture was stirred at room temperature for 2 hours and concentrated by rotary evaporation. The residue was purified by regular phase chromatography to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 8.90 (s, 1H), 8.57 (d, J=2.1 Hz, 1H), 8.48 (dd, J=4.8, 1.6 Hz, 1H), 7.91-7.82 (m, 3H), 7.71-7.64 (m, 2H), 7.41 (ddd, J=7.9, 4.7, 0.8 Hz, 1H), 4.42 (t, J=8.4 Hz, 2H), 4.05-3.96 (m, 2H), 3.89 (dt, J=8.1, 7.0 Hz, 1H), 3.81 (s, 1H); MS (ESI(+)) m/e 312 (M+H).

Workup

  1. concentrationconcentrated by rotary evaporation
  2. customThe residue was purified by regular phase chromatography

Sources & evidence

ORD record
ord-90718ba2491644a89cc0314f0c86b51c
Source dataset
uspto-grants-2016_03
Patent number
US09296723B2

Reaction notes

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