Diisopropylethylamine → 3-tert-butoxy-N-[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-benzamide

HRID 1641237ノート

反応式

HRID 1641237 の反応式
[C:1]([O:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=O)([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[N:48]1([CH2:54][CH2:55][O:56][C:57]2[C:66]3[C:61](=[CH:62][CH:63]=[CH:64][CH:65]=3)[C:60]([NH2:67])=[CH:59][CH:58]=2)[CH2:53][CH2:52][O:51][CH2:50][CH2:49]1>CN(C)C=O.O>[C:1]([O:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([NH:67][C:60]1[C:61]2[C:66](=[CH:65][CH:64]=[CH:63][CH:62]=2)[C:57]([O:56][CH2:55][CH2:54][N:48]2[CH2:49][CH2:50][O:51][CH2:52][CH2:53]2)=[CH:58][CH:59]=1)=[O:11])([CH3:2])([CH3:3])[CH3:4]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 5865983-(Tert-butoxy)benzoic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 110439124-(2-Morpholinoethoxy)naphthalen-1-amine

生成物 1

HCID 595534743-tert-butoxy-N-[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-benzamide収率 42.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of 3-tert-butoxy-benzoic acid (0.15 g, 0.774 mmol) in dimethylformamide (5 ml) is added HBTU (0.44 g, 1.5 eq) followed by the addition of diisopropylethylamine (0.296 ml, 3.0 eq). The mixture is stirred at room temperature for five minutes. A solution of 4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-ylamine (0.21 g) in dimethylformamide (2 ml) is then added. This mixture is stirred at room temperature for 15 h, diluted with water and extracted with ethyl acetate. The organic layer is washed with water, dried over Na2SO4 and evaporated. The residue is purified by column chromatography on silica gel (ethyl acetate) to give 3-tert-butoxy-N-[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-benzamide (0.146 g). Mp: 50-51° C. 1H NMR (300 MHz, DMSO-d6) δ 10.25 (s, 1H), 8.22 (m, 1H), 7.85 (m, 2H), 7.66 (s, 1H), 7.55 (m, 2H), 7.23 (d, J=7.5 Hz, 1H), 7.03 (d, J=8.1 Hz, 1H), 4.31 (t, J=5.1 Hz, 2H), 3.61 (t, J=4.2 Hz, 4H), 2.89 (brs, 2H), 2.58 (brs, 4H), 1.35 (s, 9H). MS: 449 (M+1).

後処理

  1. stirringThis mixture is stirred at room temperature for 15 h
  2. extractionextracted with ethyl acetate
  3. washThe organic layer is washed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue is purified by column chromatography on silica gel (ethyl acetate)

出典と根拠

ORDレコード
ord-52c4335aff1740cda27500e990a76fd4
出典データセット
uspto-grants-2012_02
特許番号
US08114873B2

反応ノート

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