Isopropyl isocyanate → HCID 68731859, compound

HRID 1615254Notes

Reaction equation

HRID 1615254 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[CH2:7]2.CCN(C(C)C)C(C)C.[N:21]([CH:24]([CH3:26])[CH3:25])=[C:22]=[O:23]>C1COCC1>[CH:24]([NH:21][C:22]([NH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[CH2:7]2)=[O:23])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 61277Isopropyl isocyanateHCID 81531DiisopropylethylamineHCID 64233127-aminoindolin-2-one

Product 1

HCID 68731859HCID 68731859, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 7-aminoindolin-2-one (60 mg, 0.41 mmol) in THF (3 mL) was added DIPEA (0.28 mL, 1.62 mmol), and 2-isocyanatopropane (0.05 mL, 0.49 mmol). The mixture was stirred at rt overnight then filtered. The filter cake was washed with diethyl ether to give the title compound as a pale solid (57.3 mg, 61%). 1H NMR (400 MHz, CD3OD) δ 7.09-7.04 (m, 2H), 6.99-6.95 (m, 1H), 3.57 (s, 2H), 2.64 (m, 1H), 1.20 (d, 6H, J=6.4 Hz). MS ESI [M+H]+, calcd for [C12H15N3O2+H]+ 234.12; found m/z 234.0.

Workup

  1. filtrationthen filtered
  2. washThe filter cake was washed with diethyl ether

Sources & evidence

ORD record
ord-e0dc6abe26d04861b0b0710ddfa45f4e
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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