Potassium Phosphate, Tribasic → HCID 58266416, Verbindung

HRID 1505973Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1505973
C1(S([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:20]#[N:21])=[C:18]([OH:19])[C:13]=3[C:12]3[CH:22]=[C:23]([C:26]4[CH:31]=[CH:30][C:29]([CH2:32][N:33]5[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]5)=[CH:28][CH:27]=4)[CH:24]=[N:25][C:11]2=3)(=O)=O)C=CC=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[OH-].[K+].CO.O>[OH:19][C:18]1[C:13]2[C:12]3[CH:22]=[C:23]([C:26]4[CH:31]=[CH:30][C:29]([CH2:32][N:33]5[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]5)=[CH:28][CH:27]=4)[CH:24]=[N:25][C:11]=3[NH:10][C:14]=2[CH:15]=[N:16][C:17]=1[C:20]#[N:21]

Komponenten

6

Edukt 2

HCID 62657Potassium Phosphate, TribasicHCID 58266539HCID 58266539, Verbindung

Produkt 1

HCID 58266416HCID 58266416, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 14797Potassium HydroxideLösungsmittel

Versuchsvorschrift

9-Benzenesulfonyl-5-hydroxy-3-(4-piperidin-1-ylmethylphenyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (50 mg, 0.01 mmol) was dissolved in 0.15N potassium hydroxide solution in methanol (7 mL). The reaction mixture was stirred for 2.5 h then treated with a solution of monobasic potassium phosphate (136 mg, 1.0 mmol) in water (2 mL). The resultant mixture was concentrated in vacuo and the resultant residue was diluted with water (5 mL). The pH of the aqueous phase was adjusted to 7 by the addition of 1N hydrochloric acid. The aqueous phase was extracted with ethyl acetate, DCM and THF. The combined organic phase was concentrated in vacuo and the residue purified by flash chromatography (silica, 500 mg column, Si-SPE, 10-20% methanol in DCM) to afford the title compound as its hydrochloride salt (25 mg, 63%). 1H NMR (DMSO-D6, 400 MHz): 12.91 (s, 1H), 11.86 (br. s, 1H), 10.41 (s, 1H), 9.13 (d, J=2.2 Hz, 1H), 9.00 (d, J=2.2 Hz, 1H), 8.60 (s, 1H), 7.93 (d, J=8.1 Hz, 2H), 7.76 (d, J=8.1 Hz, 2H), 4.33 (d, J=5.2 Hz, 2H), 3.39-3.29 (m, 2H), 2.92-2.83 (m, 2H), 1.85-1.63 (m, 5H), 1.45-1.31 (m, 1H). LCMS (Method A): RT=5.32 min, M+H+=384.

Aufarbeitung

  1. concentrationThe resultant mixture was concentrated in vacuo
  2. additionthe resultant residue was diluted with water (5 mL)
  3. additionThe pH of the aqueous phase was adjusted to 7 by the addition of 1N hydrochloric acid
  4. extractionThe aqueous phase was extracted with ethyl acetate, DCM and THF
  5. concentrationThe combined organic phase was concentrated in vacuo
  6. customthe residue purified by flash chromatography (silica, 500 mg column, Si-SPE, 10-20% methanol in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-8ef6c30eb6c044199b7a4c460784f206
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216980B2

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