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

HRID 533262ノート

反応式

HRID 533262 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 63651,1-Dichloroethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-760ae756ff294ccf82eae14486c1f4a7
出典データセット
uspto-grants-2014_10
特許番号
US08853209B2

反応ノート

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