Morpholine → 4-(2-Methylphenyl)-3-(morpholin-4-ylmethyl)-1-(3-(1-naphthyloxy)propyl)-1h-indole-2-carboxylic acid

HRID 1013304Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1013304
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[N:5]([CH2:19][CH2:20][CH2:21][O:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)[C:4]=1[C:33]([O:35]C)=[O:34])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH:51]1[CH2:56][CH2:55][O:54][CH2:53][CH2:52]1>ClC(Cl)C.C(OCC)(=O)C>[CH3:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[C:3]([CH2:1][N:51]1[CH2:56][CH2:55][O:54][CH2:53][CH2:52]1)=[C:4]([C:33]([OH:35])=[O:34])[N:5]2[CH2:19][CH2:20][CH2:21][O:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1

Komponenten

6

Edukt 3

HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 87353147Methyl 3-formyl-1-(3-(naphthalen-1-yloxy)propyl)-4-o-tolyl-1h-indole-2-carboxylate

Produkt 1

HCID 251001284-(2-Methylphenyl)-3-(morpholin-4-ylmethyl)-1-(3-(1-naphthyloxy)propyl)-1h-indole-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 63651,1-DichloroethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of EXAMPLE 107C (50 mg) in dichloroethane (3 ml) was added sodium triacetoxyborohydride (35 mg) and morpholine (15 mg). The mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate (200 ml) and washed with water, brine, and dried over Na2SO4. The residue was dissolved in tetrahydrofuran (4 ml), methanol (2 mL) and water (2 ml) and LiOH (100 mg) was added. The mixture was stirred at room temperature overnight. The mixture was concentrated and the residue neutralized with aqueous NH4Cl and extracted with ethyl acetate (100 mL×3). The combined extracts were dried and concentrated to give crude product, which was purified by RPHPLC. 1H NMR (300 MHz, dimethyl sulfoxide-d6) δ 8.25 (m, 1H), 7.86 (m, 2H), 7.45 (m, 9H), 6.93 (m, 2H), 4.99 (m, 2H), 4.47 (m, 1H), 4.25 (t, 2H), 3.60 (m, 10H), 2.43 (m, 2H), 1.92 (s, 3H).

Aufarbeitung

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. dissolutionThe residue was dissolved in tetrahydrofuran (4 ml)
  4. additionmethanol (2 mL) and water (2 ml) and LiOH (100 mg) was added
  5. stirringThe mixture was stirred at room temperature overnight
  6. concentrationThe mixture was concentrated
  7. extractionextracted with ethyl acetate (100 mL×3)
  8. customThe combined extracts were dried
  9. concentrationconcentrated
  10. customto give crude product, which
  11. customwas purified by RPHPLC

Quellen und Nachweise

ORD-Eintrag
ord-6bbd6301d77a48e79f6044fea98be1bd
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981888B2

Notizen zur Reaktion

Wird geladen…