Methylamine → (S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-((methylamino)methyl)quinolin-6-yl)ethyl pivalate

HRID 931756Notes

Reaction equation

HRID 931756 reaction equation
[C:1]([O:7][CH2:8][C@H:9]([C:15]1[C:16](Br)=[C:17]2[C:22](=[CH:23][C:24]=1[CH3:25])[N:21]=[C:20]([CH2:26][N:27]([CH3:29])C)[CH:19]=[CH:18]2)[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C(O[C@@H](C1C([C:58]2[CH:63]=[CH:62][C:61]([Cl:64])=[CH:60][CH:59]=2)=C2C(=CC=1C)[N+]([O-])=C(C)C=C2)COC(=O)C(C)(C)C)(C)(C)C.CN>>[C:1]([O:7][CH2:8][C@@H:9]([O:10][C:11]([CH3:13])([CH3:14])[CH3:12])[C:15]1[C:16]([C:58]2[CH:63]=[CH:62][C:61]([Cl:64])=[CH:60][CH:59]=2)=[C:17]2[C:22](=[CH:23][C:24]=1[CH3:25])[N:21]=[C:20]([CH2:26][NH:27][CH3:29])[CH:19]=[CH:18]2)(=[O:6])[C:2]([CH3:3])([CH3:4])[CH3:5]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 66631094(S)-6-(1-tert-Butoxy-2-(pivaloyloxy)ethyl)-5-(4-chlorophenyl)-2,7-dimethylquinoline 1-oxideHCID 66631121(S)-2-(5-bromo-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)-2-tert-butoxyethyl pivalate

Product 1

HCID 66631400(S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-((methylamino)methyl)quinolin-6-yl)ethyl pivalate

Procedure

Following the procedure used to prepare compound (S)-2-(5-bromo-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)-2-tert-butoxyethyl pivalate of Example 9, except that (S)-6-(1-tert-butoxy-2-(pivaloyloxy)ethyl)-5-(4-chlorophenyl)-2,7-dimethylquinoline 1-oxide was used instead of (S)-5-bromo-6-(1-tert-butoxy-2-(pivaloyloxy)ethyl)-2,7-dimethylquinoline 1-oxide, and methylamine solution was used instead of N,N-dimethylamine solution. LCMS-ESI+ (m/z): 497.3, 499.3 (M+H)+.

Sources & evidence

ORD record
ord-150ccb98a7b1446f9b30a68acdb58c70
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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