2-oxaspiro[4.4]nonane-1,3-dione → 1-[2-(4-{4-[(4,5-Dichloro-1-ethyl-1H-indole-2-carbonyl)-amino]-phenyl}-piperidin-1-yl)-2-oxo-ethyl]-cyclopentanecarboxylic acid

HRID 1645356Notes

Reaction equation

HRID 1645356 reaction equation
C(OC1C=CC=C2C=1C=C(C(NC1C=CC(C3CCN(C(=O)CC(C)(C)C(O)=O)CC3)=CC=1)=O)N2CC)C.[NH:39]1[CH2:44][CH2:43][CH:42]([C:45]2[CH:50]=[CH:49][C:48]([NH:51][C:52]([C:54]3[N:55]([CH2:65][CH3:66])[C:56]4[C:61]([CH:62]=3)=[C:60]([Cl:63])[C:59]([Cl:64])=[CH:58][CH:57]=4)=[O:53])=[CH:47][CH:46]=2)[CH2:41][CH2:40]1.[C:67]1(=[O:77])[C:71]2([CH2:75][CH2:74][CH2:73][CH2:72]2)[CH2:70][C:69](=[O:76])[O:68]1>>[Cl:63][C:60]1[C:59]([Cl:64])=[CH:58][CH:57]=[C:56]2[C:61]=1[CH:62]=[C:54]([C:52]([NH:51][C:48]1[CH:49]=[CH:50][C:45]([CH:42]3[CH2:41][CH2:40][N:39]([C:69](=[O:76])[CH2:70][C:71]4([C:67]([OH:77])=[O:68])[CH2:75][CH2:74][CH2:73][CH2:72]4)[CH2:44][CH2:43]3)=[CH:46][CH:47]=1)=[O:53])[N:55]2[CH2:65][CH3:66]

Participants

4

Reactant 3

HCID 27371022-oxaspiro[4.4]nonane-1,3-dioneHCID 593651354-(4-{4-[(4-ethoxy-1-ethyl-1H-indole-2-carbonyl)-amino]-phenyl}-piperidin-1-yl)-2,2-dimethyl-4-oxo-butyric acidHCID 667726954,5-dichloro-1-ethyl-1H-indole-2-carboxylic acid (4-piperidin-4-yl-phenyl)-amide

Product 1

HCID 593651611-[2-(4-{4-[(4,5-Dichloro-1-ethyl-1H-indole-2-carbonyl)-amino]-phenyl}-piperidin-1-yl)-2-oxo-ethyl]-cyclopentanecarboxylic acid

Procedure

With a method similar to that used for the preparation of 4-(4-{4-[(4-ethoxy-1-ethyl-1H-indole-2-carbonyl)-amino]-phenyl}-piperidin-1-yl)-2,2-dimethyl-4-oxo-butyric acid, 1-[2-(4-{4-[(4,5-dichloro-1-ethyl-1H-indole-2-carbonyl)-amino]-phenyl}1-piperidin-1-yl)-2-oxo-ethyl]cyclopentanecarboxylic acid was prepared from 4,5-dichloro-1-ethyl-1H-indole-2-carboxylic acid (4-piperidin-4-yl-phenyl)-amide and 2-oxa-spiro[4,4]nonane-1,3-dione. LCMS for C30H33Cl2N3O4 calcd. (m/e) 569, observed 570 (M+H).

Sources & evidence

ORD record
ord-6a3c6fb4ac09449895abb78276234251
Source dataset
uspto-grants-2012_02
Patent number
US08124766B2

Reaction notes

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