3-Bromophenyl isocyanate → HCID 178521886, compound

HRID 2203277Notes

Reaction equation

HRID 2203277 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.[Br:23][C:24]1[CH:25]=[C:26]([N:30]=[C:31]=[O:32])[CH:27]=[CH:28][CH:29]=1>>[Br:23][C:24]1[CH:25]=[C:26]([NH:30][C:31]([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:32])[CH:27]=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 1410013-Bromophenyl isocyanateHCID 178507413HCID 178507413, compound

Product 1

HCID 178521886HCID 178521886, compoundYield 66.2%

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 3-bromophenyl isocyanate (0.0095 mL, 0.076 mmol) were reacted to give the title compound as an off-white solid (22.4 mg, 66%). 1H NMR (DMSO-d6) δ: 10.69 (s, 1H), 8.85 (s, 1H), 8.72 (s, 1H), 7.97-7.99 (m, 1H), 7.85 (t, J=1.9 Hz, 1H), 7.42-7.45 (m, 3H), 7.29-7.31 (m, 1H), 7.21-7.27 (m, 3H), 7.13-7.15 (m, 1H), 7.05-7.08 (m, 1H), 7.01 (d, J=7.9 Hz, 1H), 4.20-4.24 (m, 1H), 3.70-3.75 (m, 1H), 3.52-3.59 (m, 2H), 2.94-3.00 (m, 1H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-cdfadea4d2ee49dab3b0274042a1f4b2
Source dataset
uspto-grants-2016_06
Patent number
US09365575B2

Reaction notes

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