5-Aminoindole → N-(1H-indol-5-yl)-2-(3-methyl-1-piperidinyl)-4-(trifluoromethyl)-5-oxazolecarboxamide

HRID 1020368Notes

Reaction equation

O[C:2]1([C:32]2C=CC=CC=2)[CH2:7][CH2:6][N:5]([C:8]2N=C[C:11]([NH:14][C:15]([C:17]3[O:21][C:20]([N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[N:19][C:18]=3[C:28]([F:31])([F:30])[F:29])=[O:16])=[CH:10][CH:9]=2)CC1.N[C:39]1C=C2C(=CC=1)NC=C2>>[NH:5]1[C:8]2[C:2](=[CH:32][C:11]([NH:14][C:15]([C:17]3[O:21][C:20]([N:22]4[CH2:27][CH2:26][CH2:25][CH:24]([CH3:39])[CH2:23]4)=[N:19][C:18]=3[C:28]([F:31])([F:29])[F:30])=[O:16])=[CH:10][CH:9]=2)[CH:7]=[CH:6]1

Participants

Reactant 2

HCID 788675-Aminoindole

HCID 46208786N-[6-(4-hydroxy-4-phenylpiperidin-1-yl)pyridin-3-yl]-2-(piperidin-1-yl)-4-(trifluoromethyl)oxazole-5-carboxamide

Product 1

HCID 67391262N-(1H-indol-5-yl)-2-(3-methyl-1-piperidinyl)-4-(trifluoromethyl)-5-oxazolecarboxamide

Procedure

Compound 44 was prepared by the general procedure for compound 1, by using intermediates A-10 and 5-aminoindole as starting materials. 1H NMR (500 MHz, DMSO-d6) δ 11.10 (br s, 1H), 10.01 (s, 1H), 7.36 (m, 2H), 7.30 (br d, 1H, J=6.8 Hz), 6.41 (s, 1H), 4.12 (m, 2H), 3.29 (br s, 1H), 3.05 (t, 1H, J=12.3 Hz), 2.74 (t, 1H, J=12.2 Hz), 1.70 (m, 3H), 1.53 (m, 1H), 1.15 (m, 1H), 0.94 (d, 3H, J=6.0 Hz). MS (M+1): 393.

Sources & evidence

ORD record: ord-d54f602691874a5c9ce953313281eb91
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716312B2

Reaction notes

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