2-Imidazolidinone → HCID 58305400, compound

HRID 1805356Notes

Reaction equation

HRID 1805356 reaction equation
[CH2:1]1[NH:6][C:4](=[O:5])[NH:3][CH2:2]1.C[O:8][C:9](=[O:18])[C:10]1[CH:15]=[C:14](I)[CH:13]=[CH:12][C:11]=1Br.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C@H:26]2[C@:28]3([C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[NH:30][C:29]3=[O:37])[CH2:27]2)=[CH:22][CH:21]=1>>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C@@H:26]2[C@@:28]3([C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]([C:14]4[CH:15]=[C:10]([CH:11]=[C:12]([N:3]5[CH2:2][CH2:1][NH:6][C:4]5=[O:5])[CH:13]=4)[C:9]([OH:8])=[O:18])[C:29]3=[O:37])[CH2:27]2)=[CH:24][CH:25]=1

Participants

4

Reactant 3

HCID 84532-ImidazolidinoneHCID 50998202Methyl 2-bromo-5-iodobenzoateHCID 67232941(1S,2S)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 58305400HCID 58305400, compound

Procedure

The title compound was prepared in analogy to Example 92 starting from ethyleneurea (commercially available), bromo-5-iodo-benzoic acid methyl ester prepared as in Example 92, (1R,2R) and (1S,2S)-2-(4-chlorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one prepared as in Scheme 1. LC/MS m/e calcd. for C26H20ClN3O4: 473, observed (M+H)+: 474.21H NMR (400 MHz, DMSO-d6) δppm 2.14 (dd, J=9.22, 4.93 Hz, 1 H) 2.41 (dd, J=7.96, 4.67 Hz, 1 H) 3.22-3.28 (m, 1 H) 3.43-3.49 (m, 1 H) 3.92-3.98 (m, 1 H) 6.19 (d, J=7.58 Hz, 1 H) 6.80 (t, J=7.71 Hz, 1 H) 6.85 (d, J=7.83 Hz, 1 H) 7.12 (t, J=8.34 Hz, 1 H) 7.22 (s, 1 H) 7.42 (q, J=8.59 Hz, 3 H) 7.64 (s, 1 H) 7.99 (t, J=2.02 Hz, 1 H) 8.13 (s, 1 H).

Sources & evidence

ORD record
ord-90538bb24681426db80b9e8f624e0496
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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