Water → HCID 11772784, compound

HRID 858034Notes

Reaction equation

[O:1]=[C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][N:3]1[CH2:11][CH2:12]OS(C1C=CC(C)=CC=1)(=O)=O.[NH:24]1[CH2:29][CH:28]=[C:27]([C:30]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[NH:32][CH:31]=2)[CH2:26][CH2:25]1.C(N(CC)CC)C.O>CS(C)=O>[NH:32]1[C:33]2[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:30]([C:27]2[CH2:28][CH2:29][N:24]([CH2:12][CH2:11][N:3]3[C:2](=[O:1])[N:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:5]4=[N:4]3)[CH2:25][CH:26]=2)=[CH:31]1

Participants

Conditions

Temperature: 85 °C

Procedure

Toluene-4-sulfonic acid 2-(3-oxo-[1,2,4]triazolo[4,3-a]pyridin-2-yl)-ethyl ester 166 mg (0.5 mmol) was dissolved in 50 ml DMSO. To this solution was added 99 mg of 3-(1,2,3,6-Tetrahydro-pyridin-4-yl)-1H-indole, (1 eq, 0.5 mmol) and 5 ml triethyl amine. The reaction media was heated under nitrogen at 85° C. for 18 hours. It was then cooled down to room temperature and poured into about 300 ml water and extracted with ethyl acetate (2×200 ml). The combined organic layers were dried over magnesium sulfate and filtered and concentrated. Flash column chromatography using ethyl acetate and 20% methanol/ethyl acetate yielded 54 mg product (30%). mp:170.4° C.; M+:360.1; H-NMR: 8.28 (b, 1H, NH), 7.88 (d, 1H), 7.55 (d, 1H), 7.30 (d, 1H), 7.14 (m, 5H), 6.47 (m, 1H), 6.19 (m, 1H), 4.25 (m, CH2), 3.35 (d, CH2), 3.00 (t, CH2) 2.86 (t, CH2), 2.60 (m, CH2).

Workup

customThe reaction media
temperatureIt was then cooled down to room temperature
extractionextracted with ethyl acetate (2×200 ml)
dry with materialThe combined organic layers were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-3034fa404bf545099e18507614a88104
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148235B2

Reaction notes

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