HCID 53244689, compound → HCID 178428620, compound

HRID 1805319Notes

Reaction equation

HRID 1805319 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH2:7])[NH:4][N:3]=1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]2[C@:17]3([C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]([CH2:26][C:27]4[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=4)[C:30](O)=[O:31])[C:18]3=[O:36])[CH2:16]2)=[CH:11][CH:10]=1>>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]2[C@:17]3([C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]([CH2:26][C:27]4[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=4)[C:30]([NH:7][C:5]4[NH:4][N:3]=[C:2]([CH3:1])[CH:6]=4)=[O:31])[C:18]3=[O:36])[CH2:16]2)=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 53244689HCID 53244689, compoundHCID 178418690HCID 178418690, compound

Product 1

HCID 178428620HCID 178428620, compound

Procedure

The title compound was prepared in analogy to Example 60 starting from 3-methyl-1 H-pyrazol-5-amine, (3-bromomethyl)-benzoate (commercially available), racemic (1R,2S) and (1S,2R)-3-((2-(4-chlorophenyl)-2′-oxospiro[cyclopropane-1,3′-indoline]-1′-yl)methyl)benzoic acid prepared as in Scheme 1. LC/MS m/e calcd. for C28H23ClN4O2: 482, observed (M+H)+: 483.21H NMR (400 MHz, MeOD-d4) δppm 2.23 (d, J=8.59 Hz, 2 H) 2.55 (s, 3 H) 3.26-3.32 (m, 1 H) 5.08-5.23 (m, 2 H) 5.85 (d, J=1.01 Hz, 1 H) 6.08 (d, J=7.07 Hz, 1 H) 6.73 (t, J=7.58 Hz, 1 H) 6.94 (d, J=7.83 Hz, 1 H) 7.07-7.14 (m, 1 H) 7.19 (d, J=8.08 Hz, 2 H) 7.30 (d, J=8.59 Hz, 2 H) 7.48 (t, J=7.71 Hz, 1 H) 7.58 (d, J=8.34 Hz, 1 H) 7.80 (d, J=7.83 Hz, 1 H) 7.85 (s, 1 H).

Sources & evidence

ORD record
ord-7e47eea998134dcca0bd135ad40380ac
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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