Hydrochloric Acid → 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-((4-phenylpiperazin-1-yl)methyl)thiazole-4-carboxylic acid

HRID 1518346

Reaktionsgleichung

Reaktionsgleichung von HRID 1518346
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10](COCC[Si](C)(C)C)[C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][C:25]([CH2:32][N:33]3[CH2:38][CH2:37][N:36]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[CH2:35][CH2:34]3)=[C:26]([C:28]([O:30]C)=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12].Cl.CCOCC>C(Cl)Cl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][C:25]([CH2:32][N:33]3[CH2:34][CH2:35][N:36]([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[CH2:37][CH2:38]3)=[C:26]([C:28]([OH:30])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 59447670methyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-((4-phenylpiperazin-1-yl)methyl)thiazole-4-carboxylate

Produkt 1

HCID 468364342-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-((4-phenylpiperazin-1-yl)methyl)thiazole-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Compound 62A (50 mg, 0.066 mmol) in DCM (3.5 ml) was treated with 2 N hydrogen chloride in ether (3.31 ml, 6.62 mmol) for 30 min. The reaction was concentrated and the residue was dissolved in THF (3 ml) and methanol (3 ml). NaOH (10% aq., 1 ml) was added. The resulting mixture was stirred overnight and concentrated. The residue was purified by purified by reverse phase HPLC (mobile phase: 0%-70% acetonitrile in 0.1% TFA aqueous solution during 40 min) to provide the title compound: 1H NMR (400 MHz, DMSO-D6) δ ppm 12.91 (1H, s), 8.02 (1H, d), 7.78 (1H, d), 7.70 (1H, d), 7.44-7.50 (2H, m), 7.41 (1H, t), 7.35 (1H, t), 7.20-7.27 (2H, m), 6.96 (2H, d), 6.84 (1H, t), 4.89 (2H, s), 4.73 (2H, s), 3.82 (2H, t), 3.45 (8H, s), 3.07 (2H, t). LCMS (APCI) m/e 611 (M+H).

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. dissolutionthe residue was dissolved in THF (3 ml)
  3. additionNaOH (10% aq., 1 ml) was added
  4. concentrationconcentrated
  5. customThe residue was purified
  6. customby purified by reverse phase HPLC (mobile phase: 0%-70% acetonitrile in 0.1% TFA aqueous solution during 40 min)

Quellen und Nachweise

ORD-Eintrag
ord-48b300441da540a284a318b797d96ddb
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232273B2

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