Dimethylamine → HCID 58305345, compound

HRID 1805368Notes

Reaction equation

CO[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10]Br)[CH:5]=1.[CH3:13][NH:14][CH3:15].CN.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C@@H:25]2[C@:27]3([C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[NH:29][C:28]3=[O:36])[CH2:26]2)=[CH:21][CH:20]=1>>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([C@H:25]2[C@@:27]3([C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[N:29]([CH2:10][C:6]4[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=4)[C:3]([N:14]([CH3:15])[CH3:13])=[O:12])[C:28]3=[O:36])[CH2:26]2)=[CH:23][CH:24]=1

Participants

Reactant 4

HCID 674Dimethylamine

HCID 6329Methylamine

HCID 517981Methyl 3-(bromomethyl)benzoate

HCID 58305285(1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 58305345HCID 58305345, compound

Procedure

The title compound was prepared in analogy to Example 60 starting from 3-bromomethyl-benzoic acid methyl ester, dimethylamine, methylamine (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 C29H27ClN2O2: 470, observed (M+H)+: 471.2 1H NMR (400 MHz, MeOD-d4) δppm 2.15-2.24 (m, 2 H) 2.90 (s, 3 H) 3.06 (s, 3 H) 3.21-3.35 (m, 1 H) 5.09 (s, 2 H) 6.05 (d, J=7.58 Hz, 1 H) 6.69 (t, J=7.58 Hz, 1 H) 6.89 (d, J=8.08 Hz, 1 H) 7.01-7.10 (m, 1 H) 7.19 (d, J=8.59 Hz, 2 H) 7.25-7.38 (m, 4 H) 7.40-7.49 (m, 2 H).

Sources & evidence

ORD record: ord-49861816e11c4e89923762fa3bb82542
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354443B2

Reaction notes

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