5-tert-butyl-2,3-dihydro-1H-inden-1-amine → N-(5-tert-butyl-2,3-dihydro-1H-inden-1-yl)-N'-5-isoquinolinylurea

HRID 912632Notes

Reaction equation

HRID 912632 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH:10]([NH2:14])[CH2:9][CH2:8]2)([CH3:4])([CH3:3])[CH3:2].[N:15]([C:18]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[CH:20]=[CH:21][N:22]=[CH:23]2)=[C:16]=[O:17]>C(OCC)C>[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH:10]([NH:14][C:16]([NH:15][C:18]1[CH:27]=[CH:26][CH:25]=[C:24]3[C:19]=1[CH:20]=[CH:21][N:22]=[CH:23]3)=[O:17])[CH2:9][CH2:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 115066015-tert-butyl-2,3-dihydro-1H-inden-1-amineHCID 115863575-Isocyanatoisoquinoline

Product 1

HCID 11485180N-(5-tert-butyl-2,3-dihydro-1H-inden-1-yl)-N'-5-isoquinolinylurea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

5-tert-Butyl-2,3-dihydro-1H-inden-1-ylamine (150 mg, 1.13 mmol) in diethyl ether (10 mL) was treated with 5-isocyanatoisoquinoline in diethyl ether. The mixture was stirred for 2 hours, filtered, and the filter cake was washed with diethyl ether to provide the title compound. NMR (DMSO-d6) 1.29 (s, 9H), 1.78-1.90 (m, 1H), 2.43-2.54 (m, 1H, buried under DMSO), 2.76-3.05 (m, 2H), 5.19 (m, 1H), 7.27 (m, 2H), 7.31 (m, 1H), 7.43 (d, 1H), 7.89 (t, 1H), 8.05 (d, 1H), 8.63 (d, 1H), 8.69 (d, 1H), 9.33 (s, 1H), 9.73 (s, 1H); MS (ESI+) 360 (M+H)+; Elemental: Calculated for C23H25N3O.HCl.0.5H2O: C, 68.22; H, 6.72; N, 10.38; Found: C, 68.31; H, 6.81; N, 10.16.

Workup

  1. filtrationfiltered
  2. washthe filter cake was washed with diethyl ether

Sources & evidence

ORD record
ord-7e064caee8124e198f4dc2d637a1442f
Source dataset
uspto-grants-2011_09
Patent number
US08026256B2

Reaction notes

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