2,3-Dimethylaniline → HCID 86585360, compound

HRID 1356389Notes

Reaction equation

HRID 1356389 reaction equation
CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1.[CH3:19][C:20]1[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:21]=1[NH2:22].[C:28]([O:32][C:33]([N:35]1[CH2:48][CH2:47][C@@H:46]2[C@@H:38]([N:39]([CH2:51][C:52](O)=[O:53])[C:40]3[CH:41]=[CH:42][C:43]([Cl:50])=[C:44]([Cl:49])[C:45]=32)[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29]>C1COCC1>[Cl:50][C:43]1[CH:42]=[CH:41][C:40]2[N:39]([CH2:51][C:52]([NH:22][C:21]3[CH:23]=[CH:24][CH:25]=[C:26]([CH3:27])[C:20]=3[CH3:19])=[O:53])[C@H:38]3[CH2:37][CH2:36][N:35]([C:33]([O:32][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:34])[CH2:48][CH2:47][C@H:46]3[C:45]=2[C:44]=1[Cl:49]

Participants

5

Reactant 3

HCID 68932,3-DimethylanilineHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 86585359HCID 86585359, compound

Product 1

HCID 86585360HCID 86585360, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

EEDQ (0.57 g, 2.3 mmol) and 2,3-dimethylaniline (0.28 g, 2.3 mmol) were added to a solution of [3-(tert-butoxycarbonyl) (5aS*,10bS*)-9,10-dichloro-2,3,4,5,5a,10b-hexahydroazepino[4,5-b]indol-6(1H)-yl]acetic acid (0.80 g, 1.9 mmol) in THF (20 mL). The reaction was heated to 50° C., cooled to rt after 6 h, and concentrated. The crude product was purified via column chromatography (Biotage, 40 M) with CH2Cl2/MeOH (99: 1) followed by crystallization from EtOAc/heptane to give a white solid: mp 145.5-146.0° C.; 1H NMR (CDCl3, 300 MHz) δ 68.49 (br s, 1H), 7.31 (m, 1H), 7.21 (d, J=8.3Hz, 1H), 7.13 (m, 1H), 7.00 (d, J=7.5 Hz, 1H), 6.37 (d, J=8.4Hz, 1H), 3.89 (m, 2H), 3.78 (m, 2H), 3.66 (m, 1H), 3.58 (m, 1H), 3.33 (m, 2H), 2.34 (m, 1H), 2.27(s, 3H), 2.17 (m, 1H), 2.02 (s, 3H), 1.90 (m, 2H), 1.45 (s, 9H); IR (diffuse reflectance) 1692, 1661, 1596, 1517, 1499, 1465, 1428, 1365, 1329, 1265, 1252, 1241, 1177, 1142, 795 cm−1; MS (EI) m/z 517 (M+), 519, 315, 313, 269, 228, 226, 57, 56, 55; Anal. Calcd for C27H33Cl2N3O3: C, 62.55; H, 6.41; N, 8.10; found: C, 62.53; H, 6.43; N, 8.08.

Workup

  1. temperaturecooled to rt after 6 h
  2. concentrationconcentrated
  3. customThe crude product was purified via column chromatography (Biotage, 40 M) with CH2Cl2/MeOH (99: 1)
  4. customfollowed by crystallization from EtOAc/heptane
  5. customto give a white solid

Sources & evidence

ORD record
ord-4c3b413ce9ca4809b222e998608f9036
Source dataset
uspto-grants-2003_07
Patent number
US06586421B2

Reaction notes

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