Acetic Acid → 1-Methylethyl {(cis)-1-acetyl-2-methyl-6-[2-(1-piperidinylmethyl)-1,3-thiazol-4-yl]-1,2,3,4-tetrahydro-4-quinolinyl}carbamate

HRID 2366921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2366921
[CH3:1][CH:2]([O:4][C:5](=[O:28])[NH:6][C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[N:18]=[C:19]([CH:22]=O)[S:20][CH:21]=3)[CH:15]=2)[N:10]([C:24](=[O:26])[CH3:25])[C@@H:9]([CH3:27])[CH2:8]1)[CH3:3].[NH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:24]([N:10]1[C:11]2[C:16](=[CH:15][C:14]([C:17]3[N:18]=[C:19]([CH2:22][N:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)[S:20][CH:21]=3)=[CH:13][CH:12]=2)[C@H:7]([NH:6][C:5](=[O:28])[O:4][CH:2]([CH3:3])[CH3:1])[CH2:8][C@@H:9]1[CH3:27])(=[O:26])[CH3:25]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 866692321-Methylethyl [(cis)-1-acetyl-6-(2-formyl-1,3-thiazol-4-yl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate

Produkt 1

HCID 866692631-Methylethyl {(cis)-1-acetyl-2-methyl-6-[2-(1-piperidinylmethyl)-1,3-thiazol-4-yl]-1,2,3,4-tetrahydro-4-quinolinyl}carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-Methylethyl[(cis)-1-acetyl-6-(2-formyl-1,3-thiazol-4-yl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Intermediate 39) (21 mg, 0.052 mmol) was dissolved in dichloromethane (DCM) (1 mL), mixed with piperidine (7.77 μL, 0.078 mmol) and acetic acid (7.49 μL, 0.131 mmol) and stirred under nitrogen for 30 minutes. Sodium triacetoxyborohydride (16.63 mg, 0.078 mmol) was added and the mixture was allowed to stir under nitrogen. The mixture was loaded onto a 2 g SCX-column, eluting with MeOH (25 mL) followed by 2M MeOH/NH3 (25 mL). Product-containing fractions were evaporated to dryness to give a solid (18 mg). This was purified on a 12+M Biotage silica column, eluting with 0 to 4% 2N methanolic ammonia in DCM. Product-containing fractions were evaporated to dryness to give a clear, colourless solid (16 mg).

Aufarbeitung

  1. stirringto stir under nitrogen
  2. washeluting with MeOH (25 mL)
  3. customProduct-containing fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-3ffc1b80930c4cc18a2348ce31ed3021
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697725B2

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