Morpholine → HCID 58305353, compound

HRID 1805344Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CO[C:9](=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12](I)[CH:11]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C@@H:25]2[C@:27]3([C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[NH:29][C:28]3=[O:36])[CH2:26]2)=[CH:21][CH:20]=1>>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([C@@H:25]2[C@:27]3([C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[N:29]([C:12]4[CH:13]=[CH:14][CH:15]=[C:10]([C:9]([N:1]5[CH2:6][CH2:5][O:4][CH2:3][CH2:2]5)=[O:17])[CH:11]=4)[C:28]3=[O:36])[CH2:26]2)=[CH:23][CH:24]=1

Participants

Reactant 3

HCID 8083Morpholine

HCID 69258Methyl 3-iodobenzoate

HCID 58305285(1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 58305353HCID 58305353, compound

Procedure

The title compound was prepared in analogy to Example 85 starting from morpholine, methyl-3-iodobenzoate (commercially available), (1R,2S) and (1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one prepared as in Scheme 1. LC/MS m/e calcd. for C27H23ClN2O3: 458, observed (M+H)+: 459.1 1H NMR (400 MHz, MeOD-d4) δppm 2.34 (dd, J=8.97, 4.93 Hz, 1 H) 2.44 (dd, J=8.59, 5.05 Hz, 1 H) 3.35-3.39 (m, 1 H) 3.67 (br. s., 8 H) 6.96 (d, J=7.83 Hz, 1 H) 7.17-7.26 (m, 2 H) 7.26-7.36 (m, 5 H) 7.41 (s, 1 H) 7.46-7.52 (m, 2 H) 7.64 (t, J=7.83 Hz, 1 H).

Sources & evidence

ORD record: ord-291cf2cd8bfc4d5594c92620d5cb03c3
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354443B2

Reaction notes

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