(2-Hydroxy-4-methoxybenzyl)-5-methyl-1-(4-methylpentyl)-2-oxoindolin-3-yl benzoate → 5-Chloro-3-(2-hydroxy-4-methoxybenzyl)-1-(3-morpholinopropyl)-2-oxoindolin-3-yl benzoate

HRID 1523094Notes

Reaction equation

HRID 1523094 reaction equation
C(OC1([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=2[OH:36])C2C(=CC=C(C)C=2)N(CCCC(C)C)C1=O)(=O)C1C=CC=CC=1.[C:37]([O:45][CH:46]1[C:54]2[C:49](=[CH:50][CH:51]=[C:52]([Cl:55])[CH:53]=2)[N:48]([CH2:56][CH2:57][CH2:58][N:59]2[CH2:64][CH2:63][O:62][CH2:61][CH2:60]2)[C:47]1=[O:65])(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[C:37]([O:45][C:46]1([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=2[OH:36])[C:54]2[C:49](=[CH:50][CH:51]=[C:52]([Cl:55])[CH:53]=2)[N:48]([CH2:56][CH2:57][CH2:58][N:59]2[CH2:64][CH2:63][O:62][CH2:61][CH2:60]2)[C:47]1=[O:65])(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

3

Reactant 2

HCID 86301599(2-Hydroxy-4-methoxybenzyl)-5-methyl-1-(4-methylpentyl)-2-oxoindolin-3-yl benzoateHCID 904164975-Chloro-1-(3-morpholinopropyl)-2-oxoindolin-3-yl benzoate

Product 1

HCID 863016005-Chloro-3-(2-hydroxy-4-methoxybenzyl)-1-(3-morpholinopropyl)-2-oxoindolin-3-yl benzoate

Procedure

This compound was prepared in a similar manner to 3-(2-hydroxy-4-methoxybenzyl)-5-methyl-1-(4-methylpentyl)-2-oxoindolin-3-yl benzoate by reacting 5-chloro-1-(3-morpholinopropyl)-2-oxoindolin-3-yl benzoate with tert-butyl (2-(hydroxymethyl)-5-methoxyphenyl)carbonate. 1H-NMR δ 8.02 (dd, 2H), 7.58 (dd, 1H), 7.45 (dd, 2H), 7.26 (m, 1H), 7.22 (d, 1H), 6.87 (d, 1H), 6.51 (d, 1H), 6.42 (d, 1H), 6.26 (dd, 1H), 3.73-3.70 (m, 8H), 3.62 (m, 1H), 3.54-3.50 (2H), 3.39 (d, 1H), 2.37-2.15 (m, 6H), 1.78 (m, 2H). Calculated mass for C30H31ClN2O6, 550.19. Observed 551.1 (M+1).

Sources & evidence

ORD record
ord-f7351f624c404a2caa5869696a8289bf
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

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