Isopropyl isocyanate → HCID 67442690, compound

HRID 1400836Notes

Reaction equation

HRID 1400836 reaction equation
[NH2:1][C:2]1[CH:30]=[CH:29][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[CH:13]=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([C:22]([N:24]5[CH2:28][CH2:27][CH2:26][CH2:25]5)=[O:23])=[CH:18][CH:17]=4)[S:15][C:8]=23)=[C:4]([F:31])[CH:3]=1.[CH:32]([N:35]=[C:36]=[O:37])([CH3:34])[CH3:33]>C(Cl)Cl>[F:31][C:4]1[CH:3]=[C:2]([NH:1][C:36]([NH:35][CH:32]([CH3:34])[CH3:33])=[O:37])[CH:30]=[CH:29][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]2[CH:13]=[C:14]([C:16]3[CH:17]=[CH:18][C:19]([C:22]([N:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)=[O:23])=[CH:20][CH:21]=3)[S:15][C:8]=12

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanateHCID 58474497HCID 58474497, compound

Product 1

HCID 67442690HCID 67442690, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 126 (150 mg, 0.346 mmol) in DCM (7 mL) was added isopropyl isocyanate (265 mg, 3.11 mmol) and the reaction mixture was heated to reflux for 8 hours. The mixture was cooled to RT and concentrated. Purification by column chromatography (EtOAc) afforded the title compound 128 which was further triturated with Et2O (90 mg, 50% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.69 (s, 1H), 8.50 (d, J=5.28 Hz, 1H), 8.49 (s, 1H), 7.93 (d, J=8.41 Hz, 2H), 7.70 (m, 1H), 7.63 (d, J=8.41 Hz, 2H), 7.35 (t, J=9.19 Hz, 1H), 7.11 (m, 1H), 6.60 (d, J=5.48 Hz, 1H), 6.15 (d, J=7.63 Hz, 1H), 3.74 (m, 1H), 3.59-3.40 (m, 4H), 1.88-1.79 (m, 4H), 1.09 (d, J=6.46 Hz, 6H). MS (m/z)=519.65 (M+H)

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 8 hours
  3. concentrationconcentrated
  4. customPurification by column chromatography (EtOAc)

Sources & evidence

ORD record
ord-8c6209c1ac2e4dd894a0fb6ea8f4cd7b
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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