m-Tolyl isocyanate → HCID 178425598, compound

HRID 2203278Notes

Reaction equation

HRID 2203278 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.[C:23]1([CH3:32])[CH:28]=[CH:27][CH:26]=[C:25]([N:29]=[C:30]=[O:31])[CH:24]=1>>[CH3:32][C:23]1[CH:24]=[C:25]([NH:29][C:30]([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:31])[CH:26]=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 178507413HCID 178507413, compound

Product 1

HCID 178425598HCID 178425598, compoundYield 73.6%

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 meta-tolyl isocyanate (0.0095 mL, 0.076 mmol) were reacted to give the title compound as a pale tan solid (21.6 mg, 73%). 1H NMR (DMSO-d6) δ: 10.68 (br. s, 1H), 8.63 (s, 1H), 8.57 (s, 1H), 7.98 (dd, J=7.9, 1.2 Hz, 1H), 7.41-7.45 (m, 3H), 7.29 (s, 1H), 7.21-7.25 (m, 3H), 7.13-7.16 (m, 1H), 7.05-7.08 (m, 1H), 7.02 (d, J=7.9 Hz, 1H), 6.78 (d, J=7.3 Hz, 1H), 4.20-4.24 (m, 1H), 3.70-3.75 (m, 1H), 3.51-3.59 (m, 2H), 2.93-2.99 (m, 1H), 2.27 (s, 3H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-e0ab96d1b38f43598e26dae00cdf6172
Source dataset
uspto-grants-2016_06
Patent number
US09365575B2

Reaction notes

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