Methyl 3-(bromomethyl)benzoate → HCID 53244292, compound

HRID 1805370Notes

Reaction equation

HRID 1805370 reaction equation
[CH3:1][N:2]([CH3:11])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.CO[C:14](=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21]Br)[CH:16]=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C@@H:31]2[C@:33]3([C:41]4[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=4)[NH:35][C:34]3=[O:42])[CH2:32]2)=[CH:27][CH:26]=1>>[Cl:24][C:25]1[CH:26]=[CH:27][C:28]([C@@H:31]2[C@:33]3([C:41]4[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=4)[N:35]([CH2:21][C:17]4[CH:18]=[CH:19][CH:20]=[C:15]([C:14]([N:8]5[CH2:9][CH2:10][N:5]([CH2:4][CH2:3][N:2]([CH3:11])[CH3:1])[CH2:6][CH2:7]5)=[O:23])[CH:16]=4)[C:34]3=[O:42])[CH2:32]2)=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 517981Methyl 3-(bromomethyl)benzoateHCID 27362291-(2-(Dimethylamino)ethyl)piperazineHCID 58305285(1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 53244292HCID 53244292, compound

Procedure

The title compound was prepared in analogy to Example 60 starting from N,N-dimethyl-2-(piperazin-1-yl)ethanamine, 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 C32H35ClN4O2: 542, observed (M+H)+: 543.1 1H NMR (400 MHz, CDCl3) δppm 2.04 (dd, J=7.96, 4.67 Hz, 1 H) 2.28 (dd, J=8.97, 4.67 Hz, 1H) 2.93 (s, 6 H) 3.18 (br. s., 4 H) 3.34 (t, J=8.59 Hz, 1 H) 3.62 (br. s., 4 H) 3.87 (br. s., 4 H) 4.95 (d, J=15.92 Hz, 1 H) 5.16 (d, J=15.92 Hz, 1 H) 6.02 (d, J=7.58 Hz, 2 H) 6.70-6.84 (m, 2 H) 7.06-7.19 (m, 3 H) 7.31 (s, 1H) 7.35 (d, J=5.31 Hz, 1 H) 7.43 (d, J=6.06 Hz, 3 H).

Sources & evidence

ORD record
ord-afb332f4ea9d4086ac06462fe3b0926d
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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