Triethylamine → 8-Dimethylcarbamoyloxy-3-(4-fluorobenzoyl)-1,1-dimethyl-1,2,3,6-tetrahydroazepino[4,5-B]indole-5-carboxylic acid ethyl ester

HRID 37956

Reaktionsgleichung

Reaktionsgleichung von HRID 37956
C(OC(C1[C:12]2[NH:13][C:14]3C=CC=CC=3C=2CCNC=1)=O)C.[CH2:20]([O:22][C:23]([C:25]1[C:31]2[NH:32][C:33]3[CH:34]=[C:35]([OH:39])[CH:36]=[CH:37][C:38]=3[C:30]=2[C:29]([CH3:41])([CH3:40])[CH2:28][N:27]([C:42](=[O:51])[C:43]2[CH:48]=[CH:47][C:46]([F:49])=[C:45](F)[CH:44]=2)[CH:26]=1)=[O:24])[CH3:21].C(N(CC)CC)C.C(N=[C:63]=[O:64])CC>C(Cl)Cl>[CH2:20]([O:22][C:23]([C:25]1[C:31]2[NH:32][C:33]3[CH:34]=[C:35]([O:39][C:63](=[O:64])[N:13]([CH3:12])[CH3:14])[CH:36]=[CH:37][C:38]=3[C:30]=2[C:29]([CH3:40])([CH3:41])[CH2:28][N:27]([C:42](=[O:51])[C:43]2[CH:44]=[CH:45][C:46]([F:49])=[CH:47][CH:48]=2)[CH:26]=1)=[O:24])[CH3:21]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 61033Propyl isocyanateHCID 57467979Ethyl 1,2,3,6-tetrahydroazepino[4,5-B]indole-5-carboxylateHCID 666407133-(3,4-Difluoro-benzoyl)-8-hydroxy-1,1-dimethyl-1,2,3,6-tetrahydro-azepino[4,5-b]-indole-5-carboxylic acid ethyl ester

Produkt 1

HCID 99831678-Dimethylcarbamoyloxy-3-(4-fluorobenzoyl)-1,1-dimethyl-1,2,3,6-tetrahydroazepino[4,5-B]indole-5-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To prepare 3-(3,4-difluoro-benzoyl)-1,1-dimethyl-8-propylcarbamoyloxy)-1,2,3,6-tetrahydro-azepino[4,5-b]indole-5-carboxylic acid ethyl ester, a mixture of 3-(3,4-difluoro-benzoyl)-8-hydroxy-1,1-dimethyl-1,2,3,6-tetrahydro-azepino[4,5-b]-indole-5-carboxylic acid ethyl ester (45 mg, 0.1 mmol), triethylamine (0.1 mL), and propylisocyanate (0.2 mL) in dry DCM (5 mL) was refluxed at 60° C. for 20 hours. The solvent was removed in vacuo, and the residue was purified by preparative reverse-phase HPLC to give the title compound, which was then acylated in the manner described in Example 2A; 1H-NMR (CDCl3): δ 10.62 (1H, s), 7.76-7.73 (2H, m), 7.52-7.47 (1H, m), 7.36-7.31 (1H, m), 7.24-7.19 (1H, m), 7.16 (1H, d), 6.86 (1H, m), 5.04 (1H, t), 4.26 (2H, q), 4.09 (2H, brs), 3.25 (2H, q), 1.66-1.54 (8H, m), 1.25 (3H, t), 0.99 (3H, t). MS (ES): 526 (MH+).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by preparative reverse-phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-c6d2180a668741acb3cf3563a30fb3b3
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524704B2

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