Isopropyl isocyanate → HCID 67441812, compound

HRID 1400863Notes

Reaction equation

[NH2:1][C:2]1[CH:31]=[CH:30][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[CH:13]=[C:14]([C:16]4[N:21]=[CH:20][C:19]([CH2:22][N:23]5[CH2:28][CH2:27][CH2:26][O:25][C:24]5=[O:29])=[CH:18][CH:17]=4)[S:15][C:8]=23)=[C:4]([F:32])[CH:3]=1.[N:33]([CH:36]([CH3:38])[CH3:37])=[C:34]=[O:35]>C(Cl)Cl>[F:32][C:4]1[CH:3]=[C:2]([NH:1][C:34]([NH:33][CH:36]([CH3:38])[CH3:37])=[O:35])[CH:31]=[CH:30][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]([CH2:22][N:23]4[CH2:28][CH2:27][CH2:26][O:25][C:24]4=[O:29])=[CH:20][N:21]=3)[S:15][C:8]=12

Participants

Conditions

Temperature: 80 °C

Procedure

A reaction mixture consisting of amine 200 (100 mg, 0.222 mmol) and 2-isocyanatopropane (434 mg, 5.10 mmol) in DCM (3 mL) was heated to 80° C. in a sealed flask overnight. The mixture was then cooled to RT and purified by Biotage (SiliaFlash 12 g cartridge, 0-12% MeOH/CHCl3) to afford after the separation title compound 201 (35 mg, 29.4% yield) as beige solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.67 (s, 1H), 8.55 (d, 1H, J=1.8 Hz), 8.50 (d, 1H, J=5.3 Hz), 8.33 (s, 1H), 8.25 (d, 1H, J=8.2 Hz), 7.84 (dd, 1H, J1=2.2 Hz, J2=8.2 Hz), 7.69 (dd, J1=2.5 Hz, J2=13.7 Hz), 7.35 (t, 1H, J=9.0 Hz), 7.12-7.10 (m, 1H), 6.62 (d, 1H, J=5.1 Hz), 6.14 (d, 1H, J=7.4 Hz), 4.50 (s, 2H), 4.21 (t, 2H, J=5.1 Hz), 3.77-3.72 (m, 1H), 3.30-3.28 (m, 2H), 1.97-1.92 (m, 2H), 1.10 (s, 3H), 1.08 (s, 3H). MS: 536.4 (MH)+

Workup

temperatureThe mixture was then cooled to RT
custompurified by Biotage (SiliaFlash 12 g cartridge, 0-12% MeOH/CHCl3)
customto afford

Sources & evidence

ORD record: ord-e9a74ff973274ee39b6c17822df960ac
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906852B2

Reaction notes

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