1-Isocyanato-4-methoxybenzene → HCID 178492396, compound

HRID 2203280Notes

Reaction equation

HRID 2203280 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:22][N:12]3[C:13](=[O:21])[NH:14][C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[C:11]3=[N:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]=[C:32]=[O:33])=[CH:27][CH:26]=1>>[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([CH:8]3[CH2:22][N:12]4[C:13](=[O:21])[NH:14][C:15]5[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=5[C:11]4=[N:10][CH2:9]3)=[CH:4][CH:3]=2)=[O:33])=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 794431-Isocyanato-4-methoxybenzeneHCID 178507413HCID 178507413, compound

Product 1

HCID 178492396HCID 178492396, compoundYield 81.4%

Procedure

In a manner similar to the procedure described in Example 7, 3-(4-aminophenyl)-2,3,4,7-tetrahydro-6H-pyrimido[1,2-c]quinazolin-6-one (20.2 mg, 0.069 mmol) and 4-methoxyphenyl isocyanate (0.0098 mL, 0.076 mmol) were reacted to give the title compound as an off-white solid (24.8 mg, 81%). 1H NMR (DMSO-d6) δ: 10.68 (s, 1H), 8.55 (s, 1H), 8.44 (s, 1H), 7.98 (d, J=7.0 Hz, 1H), 7.40-7.45 (m, 3H), 7.33-7.36 (m, 2H), 7.22 (d, J=8.5 Hz, 2H), 7.06 (t, J=7.6 Hz, 1H), 7.01 (d, J=8.2 Hz, 1H), 6.85-6.88 (m, 2H), 4.22 (dt, J=12.6, 3.5 Hz, 1H), 3.69-3.75 (m, 4H), 3.50-3.58 (m, 2H), 2.92-2.99 (m, 1H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-b859130cf9bc4f7e87a950ffe054f2d3
Source dataset
uspto-grants-2016_06
Patent number
US09365575B2

Reaction notes

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