5-Isocyanato-3-methylisoquinoline → N-(7-tert-butyl-3,4-dihydro-2H-chromen-4-yl)-N'-(3-methylisoquinolin-5-yl)urea

HRID 2092167Notes

Reaction equation

HRID 2092167 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([N:12]=[C:13]=[O:14])[CH:8]=[CH:7][CH:6]=2.[C:15]([C:19]1[CH:28]=[C:27]2[C:22]([CH:23]([NH2:29])[CH2:24][CH2:25][O:26]2)=[CH:21][CH:20]=1)([CH3:18])([CH3:17])[CH3:16]>>[C:15]([C:19]1[CH:28]=[C:27]2[C:22]([CH:23]([NH:29][C:13]([NH:12][C:9]3[CH:8]=[CH:7][CH:6]=[C:5]4[C:10]=3[CH:11]=[C:2]([CH3:1])[N:3]=[CH:4]4)=[O:14])[CH2:24][CH2:25][O:26]2)=[CH:21][CH:20]=1)([CH3:18])([CH3:16])[CH3:17]

Participants

3

Reactant 2

HCID 222283825-Isocyanato-3-methylisoquinolineHCID 672368437-tert-Butyl-chroman-4-ylamine

Product 1

HCID 53251335N-(7-tert-butyl-3,4-dihydro-2H-chromen-4-yl)-N'-(3-methylisoquinolin-5-yl)ureaYield 64%

Procedure

6 mL of the 3-methyl-5-isocyanato-isoquinoline solution was added to the product of Example 1C (123 mg, 0.6 mmol). The reaction mixture was stirred overnight, and the percipitate formed was collected by filtration and washed with diethyl ether to give 0.15 g of the title compound (64% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 9.17 (s, 1 H), 8.46 (s, 1 H), 8.34 (d, J=6.8 Hz, 1 H), 7.66-7.73 (m, 2 H), 7.51 (t, J=8.0 Hz, 1 H), 7.25 (d, J=8.5 Hz, 1 H), 7.12 (d, J=7.1 Hz, 1 H), 6.98 (dd, J=8.0, 1.9 Hz, 1 H), 6.80 (d, J=2.0 Hz, 1 H), 4.82-4.89 (m, 1 H), 4.24-4.31 (m, 1 H), 4.10-4.18 (m, 1 H), 2.63 (s, 3 H), 1.99-2.14 (m, 2 H), 1.25 (s, 9 H). MS (ESL+) m/e 390 (M+H)+. Calc'd. For C24H27N3O2.0.5; H2O: C, 72.34; H, 7.08; N, 10.54. Found C, 72.52; H, 7.23; N, 10.53.

Workup

  1. customthe percipitate formed
  2. filtrationwas collected by filtration
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-7d216b0602bb4e988ef54495d03d85de
Source dataset
uspto-grants-2013_05
Patent number
US08440691B2

Reaction notes

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