5-chloro-1-ethyl-1H-indole-2-carboxylic acid → 5-Chloro-1-ethyl-1H-indole-2-carboxylic acid (6-piperazin-1-yl-pyridin-3-yl)-amide

HRID 1645338Notes

Reaction equation

HRID 1645338 reaction equation
[N:1]1([C:7]2[N:12]=[CH:11][C:10]([NH:13]C(C3SC4C=CC=C(Cl)C=4C=3)=O)=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[N:32]([CH2:36][CH3:37])[C:31]([C:38]([OH:40])=O)=[CH:30]2.C(OC(N1CCN(C2C=CC(N)=CN=2)CC1)=O)(C)(C)C>>[N:1]1([C:7]2[N:12]=[CH:11][C:10]([NH:13][C:38]([C:31]3[N:32]([CH2:36][CH3:37])[C:33]4[C:29]([CH:30]=3)=[CH:28][C:27]([Cl:26])=[CH:35][CH:34]=4)=[O:40])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 152903065-chloro-1-ethyl-1H-indole-2-carboxylic acidHCID 17999304tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylateHCID 593651784-Chloro-benzo[b]thiophene-2-carboxylic acid (6-piperazin-1-yl-pyridin-3-yl)-amide

Product 1

HCID 593651955-Chloro-1-ethyl-1H-indole-2-carboxylic acid (6-piperazin-1-yl-pyridin-3-yl)-amide

Procedure

With a method similar to that used for the preparation of 4-chloro-benzo[b]thiophene-2-carboxylic acid (6-piperazin-1-yl-pyridin-3-yl)-amide, 5-chloro-1-ethyl-1,4-indole-2-carboxylic acid (6-piperazin-1-yl-pyridin-3-yl)-amide was prepared from 5-chloro-1-ethyl-1H-indole-2-carboxylic acid and 4-(5-amino-pyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester. LCMS for C20H22Cl N5O calcd. (m/e) 383, observed 384 (M+H).

Sources & evidence

ORD record
ord-226e2c9f475c4921b2a85aebddd16e98
Source dataset
uspto-grants-2012_02
Patent number
US08124766B2

Reaction notes

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