N-(3-Aminopropyl)morpholine → HCID 67233484, compound

HRID 1805369Notes

Reaction equation

HRID 1805369 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][NH2:10])[CH2:3][CH2:2]1.CO[C:13](=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20]Br)[CH:15]=1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C@@H:30]2[C@:32]3([C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[NH:34][C:33]3=[O:41])[CH2:31]2)=[CH:26][CH:25]=1>>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([C@@H:30]2[C@:32]3([C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[N:34]([CH2:20][C:16]4[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=4)[C:13]([NH:10][CH2:9][CH2:8][CH2:7][N:4]4[CH2:5][CH2:6][O:1][CH2:2][CH2:3]4)=[O:22])[C:33]3=[O:41])[CH2:31]2)=[CH:28][CH:29]=1

Participants

4

Reactant 3

HCID 61055N-(3-Aminopropyl)morpholineHCID 517981Methyl 3-(bromomethyl)benzoateHCID 58305285(1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 67233484HCID 67233484, compound

Procedure

The title compound was prepared in analogy to Example 60 starting from form 3 3-morpholinopropan-1-amine, 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 C31H32ClN3O3: 529, observed (M+H)+: 530.2 1H NMR (400 MHz, MeOD-d4) δppm 2.02-2.15 (m, 2 H) 2.24 (d, J=8.59 Hz, 2 H) 3.15 (br. s., 2 H) 3.23 (d, J=8.08 Hz, 2 H) 3.25-3.31 (m, 1 H) 3.47-3.57 (m, 4 H) 3.79 (t, J=12.38 Hz, 2 H) 4.06 (br. s., 2 H) 5.14 (s, 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) 7.09 (t, J=7.71 Hz, 1 H) 7.20-7.28 (m, 2 H) 7.28-7.37 (m, 2 H) 7.49 (t, J=7.71 Hz, 1 H) 7.53-7.61 (m, 1 H) 7.78 (d, J=8.08 Hz, 1 H) 7.87 (s, 1 H).

Sources & evidence

ORD record
ord-3f3475ce1bc8419eaff76d34b30e518d
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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