Diisopropylethylamine → (4-Benzotriazol-1-yl-piperidin-1-yl)-[6-chloro-1-(2-methylamino-ethyl)-1H-indol-3-yl]-methanone hydrochloride

HRID 1097846Notes

Reaction equation

Cl.[Cl:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:16]([N:18]3[CH2:23][CH2:22][CH:21]([N:24]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)CC4=O)[CH2:20][CH2:19]3)=[O:17])=[CH:8][N:9]2[CH2:12][CH2:13][NH:14][CH3:15])=[CH:5][CH:4]=1.Cl.N1CCC([N:41]2C3C=CC=CC=3N=[N:42]2)CC1.C(N(CC)C(C)C)(C)C>>[ClH:2].[N:24]1([CH:21]2[CH2:22][CH2:23][N:18]([C:16]([C:7]3[C:6]4[C:5](=[CH:4][C:3]([Cl:2])=[CH:11][CH:10]=4)[N:9]([CH2:12][CH2:13][NH:14][CH3:15])[CH:8]=3)=[O:17])[CH2:19][CH2:20]2)[C:32]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[N:42]=[N:41]1

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 27793801-(Piperidin-4-yl)-1H-benzotriazole--hydrogen chloride (1/1)

HCID 24987660HCID 24987660, compound

Product 1

HCID 25001181(4-Benzotriazol-1-yl-piperidin-1-yl)-[6-chloro-1-(2-methylamino-ethyl)-1H-indol-3-yl]-methanone hydrochloride

Procedure

The title compound was prepared according to the procedures described for the preparation of 1-{1-[6-chloro-1-(2-methylamino-ethyl)-1H-indole-3-carbonyl]-piperidin-4-yl}-1,3-dihydro-indol-2-one hydrochloride using 1-(4-piperidyl)-1H-1,2,3-benzotriazole hydrochloride instead of 1,3-dihydro-1-(piperidin-4-yl)-(2H)-indol-2-one and a total of 3.2 molar equivalents of N,N-diisopropylethylamine instead of 2.2 molar equivalents in step a).

Sources & evidence

ORD record: ord-de484fd0a5ce4013b5d3600d2b58dc3b
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143281B2

Reaction notes

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