AM-103 free acid → 3-[1-[4-(6-methoxy-pyridin-3-yl)-benzyl]-3-(2-methyl-propane-2-sulfinyl)-5-(pyridin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethyl-propionic acid

HRID 2366100Notes

Reaction equation

HRID 2366100 reaction equation
[C:1]([S:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:13]=2)[N:8]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:31]=[N:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=3)=[CH:26][CH:25]=2)[C:7]=1[CH2:38][C:39]([CH3:44])([CH3:43])[C:40]([OH:42])=[O:41])([CH3:4])([CH3:3])[CH3:2].C(SC1C2C(=CC=C([O:59]CC3C=CC=CN=3)C=2)N(CC2C=CC(C3C=NC(O)=CC=3)=CC=2)C=1CC(C)(C)C(O)=O)(C)(C)C>>[CH3:37][O:36][C:33]1[N:32]=[CH:31][C:30]([C:27]2[CH:28]=[CH:29][C:24]([CH2:23][N:8]3[C:9]4[C:14](=[CH:13][C:12]([O:15][CH2:16][C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=5)=[CH:11][CH:10]=4)[C:6]([S:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[O:59])=[C:7]3[CH2:38][C:39]([CH3:44])([CH3:43])[C:40]([OH:42])=[O:41])=[CH:25][CH:26]=2)=[CH:35][CH:34]=1

Participants

3

Reactant 2

HCID 16224456AM-103 free acidHCID 178454935HCID 178454935, compound

Product 1

HCID 452737123-[1-[4-(6-methoxy-pyridin-3-yl)-benzyl]-3-(2-methyl-propane-2-sulfinyl)-5-(pyridin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethyl-propionic acid

Procedure

3-[3-tert-butylsulfanyl-1-[4-(6-methoxy-pyridin-3-yl)-benzyl]-5-(1-oxy-pyridin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethyl-propionic acid (M3); the acyl gluconuride of 3-[3-tert-butylsulfanyl-1-[4-(6-methoxy-pyridin-3-yl)-benzyl]-5-(pyridin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethyl-propionic acid (M4); and 3-[3-tert-butylsulfanyl-1-[4-(6-hydroxy-pyridin-3-yl)-benzyl]-5-(pyridin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethyl-propionic acid (M5; which exists also as a pyridon-5-yl tautomer).

Sources & evidence

ORD record
ord-5c88a70e4b084ec2818db28d4e4ac0eb
Source dataset
uspto-grants-2014_04
Patent number
US08697730B2

Reaction notes

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