5-chloro-1-ethyl-1H-indole-2-carboxylic acid → 5-Chloro-1-ethyl-4H-indole-2-carboxylic acid {6-[(2-methoxy-ethyl)-methyl-amino]-pyridin-3-yl}-amide hydrochloride

HRID 1645352Notes

Reaction equation

HRID 1645352 reaction equation
Cl.COCCN(C)C1N=CC(NC(C2N(CC)C3C(C=2)=CC(OC(F)(F)F)=CC=3)=O)=CC=1.Cl.[CH3:34][O:35][CH2:36][CH2:37][N:38]([CH3:60])[C:39]1[N:44]=[CH:43][C:42]([NH:45][C:46]([C:48]2[N:49]([CH2:58][CH3:59])[C:50]3[C:55]([CH:56]=2)=[CH:54][C:53]([Cl:57])=[CH:52][CH:51]=3)=[O:47])=[CH:41][CH:40]=1.ClC1C=C2C(=CC=1)N(CC)C(C(O)=O)=C2>>[ClH:57].[CH3:34][O:35][CH2:36][CH2:37][N:38]([CH3:60])[C:39]1[N:44]=[CH:43][C:42]([NH:45][C:46]([CH:48]2[CH:56]=[C:55]3[C:50](=[CH:51][CH:52]=[C:53]([Cl:57])[CH2:54]3)[N:49]2[CH2:58][CH3:59])=[O:47])=[CH:41][CH:40]=1

Participants

4

Reactant 3

HCID 152903065-chloro-1-ethyl-1H-indole-2-carboxylic acidHCID 667724081-ethyl-5-trifluoromethoxy-1H-indole-2-carboxylic acid {6-[(2-methoxy-ethyl)-methyl-amino]-pyridin-3-yl}-amide hydrochlorideHCID 667727655-chloro-1-ethyl-1H-indole-2-carboxylic acid {6-[(2-methoxy-ethyl)-methyl-amino]-pyridin-3-yl}-amide hydrochloride

Product 1

HCID 866424145-Chloro-1-ethyl-4H-indole-2-carboxylic acid {6-[(2-methoxy-ethyl)-methyl-amino]-pyridin-3-yl}-amide hydrochloride

Procedure

With a method similar to that used for the preparation of 1-ethyl-5-trifluoromethoxy-1H-indole-2-carboxylic acid {6-[(2-methoxy-ethyl)-methyl-amino]-pyridin-3-yl}-amide hydrochloride, 5-chloro-1-ethyl-1H-indole-2-carboxylic acid {6-[(2-methoxy-ethyl)-methyl-amino]-pyridin-3-yl}-amide hydrochloride was prepared from 5-chloro-1-ethyl-1H-indole-2-carboxylic acid. LCMS for C20H23ClN4O2 calcd. (m/e) 386, observed 387 (M+H).

Sources & evidence

ORD record
ord-cd84c83f71b24d27bc3ca414dd77facb
Source dataset
uspto-grants-2012_02
Patent number
US08124766B2

Reaction notes

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