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

HRID 1158804Notes

Reaction equation

HRID 1158804 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 precipitate 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, 1H), 8.46 (s, 1H), 8.34 (d, J=6.8 Hz, 1H), 7.66-7.73 (m, 2H), 7.51 (t, J=8.0 Hz, 1H), 7.25 (d, J=8.5 Hz, 1H), 7.12 (d, J=7.1 Hz, 1H), 6.98 (dd, J=8.0, 1.9 Hz, 1H), 6.80 (d, J=2.0 Hz, 1H), 4.82-4.89 (m, 1H), 4.24-4.31 (m, 1H), 4.10-4.18 (m, 1H), 2.63 (s, 3H), 1.99-2.14 (m, 2H), 1.25 (s, 9H). MS (ESI+) m/e 390 (M+H)+. Calc'd. For C24H27N3O2.0.5H2O: C, 72.34; H, 7.08; N, 10.54. Found C, 72.52; H, 7.23; N, 10.53.

Workup

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

Sources & evidence

ORD record
ord-4d91e76e06514fb2a042a4e175e04b99
Source dataset
uspto-grants-2010_10
Patent number
US07812019B2

Reaction notes

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