2-Morpholinoethylamine → HCID 53244295, compound

HRID 1805371Notes

Reaction equation

HRID 1805371 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][NH2:9])[CH2:3][CH2:2]1.CO[C:12](=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19]Br)[CH:14]=1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C@@H:29]2[C@:31]3([C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[NH:33][C:32]3=[O:40])[CH2:30]2)=[CH:25][CH:24]=1>>[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([C@@H:29]2[C@:31]3([C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[N:33]([CH2:19][C:15]4[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=4)[C:12]([NH:9][CH2:8][CH2:7][N:4]4[CH2:5][CH2:6][O:1][CH2:2][CH2:3]4)=[O:21])[C:32]3=[O:40])[CH2:30]2)=[CH:27][CH:28]=1

Participants

4

Reactant 3

HCID 4082852-MorpholinoethylamineHCID 517981Methyl 3-(bromomethyl)benzoateHCID 58305285(1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 53244295HCID 53244295, compound

Procedure

The title compound was prepared in analogy to Example 60 starting from 2-morpholinoethanamine, 3-bromomethyl-benzoic acid methyl ester (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 C30H30ClN3O3: 515, observed (M+H)+: 516.21H NMR (400 MHz, MeOD-d4) δppm 2.24 (d, J=8.59 Hz, 2 H) 3.20 (br. s., 2 H) 3.29 (s, 1 H) 3.42 (t, J=5.81 Hz, 2 H) 3.69 (br. s., 4 H) 3.80 (t, J=5.81 Hz, 2 H) 4.08 (br. s., 2 H) 5.14 (d, J=1.52 Hz, 2 H) 6.09 (d, J=7.33 Hz, 1 H) 6.73 (t, J=7.58 Hz, 1 H) 6.91 (d, J=8.08 Hz, 1 H) 7.04-7.13 (m, 1 H) 7.22-7.28 (m, 2 H) 7.29-7.36 (m, 2 H) 7.50 (t, J=7.71 Hz, 1 H) 7.55-7.62 (m, 1 H) 7.80 (d, J=7.58 Hz, 1 H) 7.90 (s, 1 H).

Sources & evidence

ORD record
ord-ae84a8172efa42b79871411720818a24
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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