2-Methylpropyl isocyanate → 4-[4-(7-Amino-2-benzo[d]isothiazol-7-yl-furo[2,3-c]pyridin-4-yl)-pyrazol-1-yl]-piperidine-1-carboxylic acid isobutyl-amide

HRID 389571

Reaktionsgleichung

Reaktionsgleichung von HRID 389571
[S:1]1[C:5]2[C:6]([C:10]3[O:30][C:13]4=[C:14]([NH2:29])[N:15]=[CH:16][C:17]([C:18]5[CH:19]=[N:20][N:21]([CH:23]6[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]6)[CH:22]=5)=[C:12]4[CH:11]=3)=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[N:2]1.C(N(C(C)C)CC)(C)C.[CH2:40]([N:44]=[C:45]=[O:46])[CH:41]([CH3:43])[CH3:42]>CN(C=O)C>[CH2:40]([NH:44][C:45]([N:26]1[CH2:25][CH2:24][CH:23]([N:21]2[CH:22]=[C:18]([C:17]3[CH:16]=[N:15][C:14]([NH2:29])=[C:13]4[O:30][C:10]([C:6]5[C:5]6[S:1][N:2]=[CH:3][C:4]=6[CH:9]=[CH:8][CH:7]=5)=[CH:11][C:12]=34)[CH:19]=[N:20]2)[CH2:28][CH2:27]1)=[O:46])[CH:41]([CH3:43])[CH3:42]

Komponenten

5

Edukt 3

HCID 612812-Methylpropyl isocyanateHCID 81531DiisopropylethylamineHCID 667599142-benzo[d]isothiazol-7-yl-4-(1-piperidin-4-yl-1H-pyrazol-4-yl)-furo[2,3-c]pyridin-7-ylamine

Produkt 1

HCID 667596174-[4-(7-Amino-2-benzo[d]isothiazol-7-yl-furo[2,3-c]pyridin-4-yl)-pyrazol-1-yl]-piperidine-1-carboxylic acid isobutyl-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-benzo[d]isothiazol-7-yl-4-(1-piperidin-4-yl-1H-pyrazol-4-yl)-furo[2,3-c]pyridin-7-ylamine (20.8 mg, 0.05 mmol) in DMF (0.5 mL) was added diisopropylethylamine (0.05 mL, 6.5 mmol) and isobutyl isocyanate (0.06 mmol). The resulting solution stirred at room temperature overnight. The mixture was concentrated and then purified by MDP to afford the title compound as an off-white solid. 1H NMR (400 MHz, CD3OD): δ 9.51 (s, 1H), 9.12 (d, J=1.5 Hz, 1H), 8.84 (d, J=7.3 Hz, 1H), 8.72 (d, J=7.3 Hz, 1H), 8.35 (s, 1H), 8.07 (s, 1H), 7.92 (s, 1H), 7.88 (s, 1H), 4.53 (m, 1H), 3.03 (m, 4H), 2.18 (m, 2H), 2.06 (m, 4H), 1.83 (m, 1H), 1.76 (d, J=5.8 Hz, 6H); MS (ESI): MS (ESI): 516.64 [M+H]+; HPLC tR=0.86 min (HPLC: Analytical—2 min).

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. custompurified by MDP

Quellen und Nachweise

ORD-Eintrag
ord-6c1130ec905043dd9500c966d7d8dade
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08378104B2

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