Methyl 3-(bromomethyl)benzoate → HCID 178521741, compound

HRID 1805373Notes

Reaction equation

HRID 1805373 reaction equation
[CH:1]1([C:4]2[CH:8]=[C:7]([NH2:9])[NH:6][N:5]=2)[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][C:7]4[NH:6][N:5]=[C:4]([CH:1]5[CH2:3][CH2:2]5)[CH:8]=4)=[O:21])[C:32]3=[O:40])[CH2:30]2)=[CH:27][CH:28]=1

Participants

4

Reactant 3

HCID 517981Methyl 3-(bromomethyl)benzoateHCID 58305285(1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-oneHCID 178507266HCID 178507266, compound

Product 1

HCID 178521741HCID 178521741, compound

Procedure

The title compound was prepared in analogy to Example 60 starting from 3-cyclopropyl-1H-pyrazol-5-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 C30H25ClN4O2: 508, observed (M+H)+: 509.21H NMR (400 MHz, MeOD-d4) δppm 0.66-0.77 (m, 2 H) 1.02 (dd, J=8.34, 1.77 Hz, 2 H) 2.24 (d, J=8.59 Hz, 2H) 2.47-2.57 (m, 1 H) 3.26-3.32 (m, 1 H) 5.07-5.25 (m, 2 H) 5.65 (s, 1 H) 6.09 (d, J=7.58 Hz, 1 H) 6.73 (t, J=7.58 Hz, 1 H) 6.96 (d, J=7.83 Hz, 1 H) 7.07-7.14 (m, 1 H) 7.20 (d, J=8.34 Hz, 2 H) 7.31 (d, J=8.34 Hz, 2H) 7.49 (t, J=7.83 Hz, 1 H) 7.55-7.63 (m, 1 H) 7.80 (d, J=7.83 Hz, 1 H) 7.83 (s, 1 H).

Sources & evidence

ORD record
ord-aa76929de26548cdac10d7756e85ab9d
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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