Trifluoroacetic acid → 4-[5-({[(3R)-1-(2-cyanobenzyl)piperidin-3-yl]amino}carbonyl)-1H-indazol-3-yl]pyridinium trifluoroacetate

HRID 1467307Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1467307
[C:1]([C:3]1[CH:52]=[CH:51][CH:50]=[CH:49][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][C@@H:8]([NH:12][C:13]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:19]=[C:18]3[C:43]2[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=2)=[O:14])[CH2:7]1)#[N:2].[C:53]([OH:59])([C:55]([F:58])([F:57])[F:56])=[O:54]>>[F:56][C:55]([F:58])([F:57])[C:53]([O-:59])=[O:54].[C:1]([C:3]1[CH:52]=[CH:51][CH:50]=[CH:49][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][C@@H:8]([NH:12][C:13]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][N:19]=[C:18]3[C:43]2[CH:44]=[CH:45][NH+:46]=[CH:47][CH:48]=2)=[O:14])[CH2:7]1)#[N:2]

Komponenten

3

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86681276N-[(3R)-1-(2-cyanobenzyl)piperidin-3-yl]-3-pyridin-4-yl-1-trityl-1H-indazole-5-carboxamide

Produkt 1

HCID 866812774-[5-({[(3R)-1-(2-cyanobenzyl)piperidin-3-yl]amino}carbonyl)-1H-indazol-3-yl]pyridinium trifluoroacetate

Versuchsvorschrift

To a microwave vial equipped with a stir bar was added N-[(3R)-1-(2-cyanobenzyl)piperidin-3-yl]-3-pyridin-4-yl-1-trityl-1H-indazole-5-carboxamide (41.7 mg, 0.061 mmol) and TFA (1000 μl, 12.98 mmol). The reaction was stirred at room temperature for 20 minutes. After 20 minutes the LCMS indicates formation of the desired product. Triethylsilane (19.62 μl, 0.123 mmol) was addes, and the crude reaction was concentrated in vacuo. The crude was dissolved in 1 ml DMSO, filtered, and purified by reverse phase chromatography. The material was concentrated, and was then dissolved in acetonitrile and water. The compound was dried on the lyophilizer over 2 days to provide fluffy white solid. LCMS calc'd for C26H25N6O [M+H]+=437; found 437 1H NMR (600 MHz, CD3OD) δ 8.9 (d, 2H), 8.9 (s, 1H), 8.7 (d, 2H), 8.0 (d, 1H), 7.9 (d, 1H), 7.8 (s, 2H), 7.8 (d, 1H), 7.7 (m, 1H), 4.6 (s, 2H), 4.4 (m, 1H), 3.7 (m, 1H), 3.6 (m, 1H), 3.2 (m, 2H), 2.2 (m, 2H), 2.0 (m, 1H), 1.8 (m, 1H).

Aufarbeitung

  1. customTo a microwave vial equipped with a stir bar
  2. waitAfter 20 minutes the LCMS indicates

Quellen und Nachweise

ORD-Eintrag
ord-759af97709a3425e8a0584b4cf8751d1
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999957B2

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