2,2-Dimethylsuccinic anhydride → 4-(4-{5-[(1-Ethyl-4-isobutoxy-1H-indole-2-carbonyl)-amino]-pyridin-2-yl}-piperazin-1-yl)-2,2-dimethyl-4-oxo-butyric acid hydrochloric acid

HRID 1645348Notes

Reaction equation

HRID 1645348 reaction equation
[Cl:1]C1C2C=C(C(NC3C=CC(N4CCN([C:26](=[O:34])[CH2:27][C:28]([CH3:33])([CH3:32])[C:29]([OH:31])=[O:30])CC4)=NC=3)=O)SC=2C=CC=1.[N:35]1([C:41]2[N:46]=[CH:45][C:44]([NH:47][C:48]([C:50]3[N:51]([CH2:64][CH3:65])[C:52]4[C:57]([CH:58]=3)=[C:56]([O:59][CH2:60][CH:61]([CH3:63])[CH3:62])[CH:55]=[CH:54][CH:53]=4)=[O:49])=[CH:43][CH:42]=2)[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1.CC1(C)CC(=O)OC1=O>C(Cl)Cl>[ClH:1].[CH2:64]([N:51]1[C:52]2[C:57](=[C:56]([O:59][CH2:60][CH:61]([CH3:62])[CH3:63])[CH:55]=[CH:54][CH:53]=2)[CH:58]=[C:50]1[C:48]([NH:47][C:44]1[CH:43]=[CH:42][C:41]([N:35]2[CH2:40][CH2:39][N:38]([C:26](=[O:34])[CH2:27][C:28]([CH3:33])([CH3:32])[C:29]([OH:31])=[O:30])[CH2:37][CH2:36]2)=[N:46][CH:45]=1)=[O:49])[CH3:65]

Participants

5

Reactant 3

HCID 870672,2-Dimethylsuccinic anhydrideHCID 462078284-(4-{5-[(4-Chloro-benzo[b]thiophene-2-carbonyl)-amino]-pyridin-2-yl}-piperazin-1-yl)-2,2-dimethyl-4-oxo-butyric acidHCID 593651891-ethyl-4-isobutoxy-1H-indole-2-carboxylic acid (6-piperazin-1-yl-pyridin-3-yl)-amide

Product 1

HCID 667724544-(4-{5-[(1-Ethyl-4-isobutoxy-1H-indole-2-carbonyl)-amino]-pyridin-2-yl}-piperazin-1-yl)-2,2-dimethyl-4-oxo-butyric acid hydrochloric acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

With a method similar to that used for the preparation of 4-(4-{5-[(4-chloro-benzo[b]thiophene-2-carbonyl)-amino]-pyridin-2-yl}-piperazin-1-yl)-2,2-dimethyl-4-oxo-butyric acid, 4-(4-{5-[(1-ethyl-4-isobutoxy-1,1-indole-2-carbonyl)-amino]-pyridin-2-yl}-piperazin-1-yl)-2,2-dimethyl-4-oxo-butyric acid was prepared from 1-ethyl-4-isobutoxy-1H-indole-2-carboxylic acid (6-piperazin-1-yl-pyridin-3-yl)-amide and 2,2-dimethylsuccinic anhydride. The desired product was dissolved in methylene chloride and treated with gaseous hydrogen chloride in ether. After the evaporation of solvents, a hydrochloride salt was obtained. LCMS for C30H39N5O5 calcd. (m/e) 549, observed 550 (M+H).

Sources & evidence

ORD record
ord-e0e12249dc0f40d980889c19ecf9d91c
Source dataset
uspto-grants-2012_02
Patent number
US08124766B2

Reaction notes

Loading…