Methyl 3-(bromomethyl)benzoate → HCID 67232432, compound

HRID 1805374Notes

Reaction equation

HRID 1805374 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH2:9])[CH: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:6]4[CH:5]=[C:4]([CH:1]5[CH2:3][CH2:2]5)[NH:8][N:7]=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 27580143-cyclopropyl-1H-pyrazol-5-amineHCID 58305285(1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 67232432HCID 67232432, compound

Procedure

The title compound was prepared in analogy to Example 60 starting from 5-cyclopropyl-1H-pyrazol-3-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)+: 509.2 1H NMR (400 MHz, MeOD-d4) δppm 0.54-0.77 (m, 2 H) 0.79-0.95 (m, 2 H) 1.62-1.77 (m, 1 H) 2.05 (s, 1H) 2.18-2.30 (m, 2 H) 3.23-3.31 (m, 1 H) 5.07-5.26 (m, 2 H) 6.09 (d, J=6.82 Hz, 1 H) 6.72 (t, J=7.58 Hz, 1H) 6.95 (d, J=7.83 Hz, 1 H) 7.05-7.14 (m, 1 H) 7.14-7.20 (m, 2 H) 7.30 (d, J=8.34 Hz, 2 H) 7.51 (t, J=7.71 Hz, 1 H) 7.62 (d, J=7.83 Hz, 1 H) 7.89 (d, J=7.83 Hz, 1 H) 7.94 (s, 1 H).

Sources & evidence

ORD record
ord-3e682d053475403e9f3e8e60b0e4ca25
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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