3-Aminopropylphosphonic acid → HCID 54670198、化合物

HRID 1893155

反応式

HRID 1893155 の反応式
[CH2:1]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:17][C:16]([CH:25]=O)=[CH:15][CH:14]=2)=[N:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH2:27][CH2:28][CH2:29][CH2:30][P:31](=[O:34])([OH:33])[OH:32].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.C([BH3-])#N.[Na+]>CO>[CH2:1]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:17][C:16]([CH2:25][NH:27][CH2:28][CH2:29][CH2:30][P:31](=[O:32])([OH:34])[OH:33])=[CH:15][CH:14]=2)=[N:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

参加物

6

反応物 4

HCID 975873-Aminopropylphosphonic acidHCID 2723671Tetrabutylammonium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 86659251HCID 86659251、化合物

生成物 1

HCID 54670198HCID 54670198、化合物収率 33.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

To a solution of 6-(5-hexylpyridin-2-yl)biphenyl-3-carbaldehyde (80 mg, 0.233 mmol) and (3-aminopropyl)phosphonic acid (32.4 mg) in methanol was added tetrabutylammonium hydroxide (1M in MeOH, 0.23 mL). The reaction mixture was heated to 50° C. for 30 min with stirring, then sodium cyanoborohydride (41 mg, 0.65 mmol) was added. The reaction mixture was heated to 50° C. with stirring for 3 h. After cooling to RT, the mixture was concentrated and purified by MPLC (0-100% ethyl acetate in hexanes) to give 36 mg of the desired product as a colorless solid. 1H NMR (300 MHz, CD3OD) δ 8.34 (d, J=1.76 Hz, 1H), 7.58-7.63 (m, 3H), 7.41 (dd, J=2.34, 8.20 Hz, 1H), 7.20-7.25 (m, 3H), 7.11-7.16 (m, 2H), 6.91 (d, J=7.91 Hz, 1H), 4.21 (s, 2H), 3.11 (t, J=6.30 Hz, 2H), 2.61 (t, J=7.62 Hz, 2H), 1.92-2.07 (m, 2H), 1.55-1.74 (m, 4H), 1.31 (br. s., 6H), 0.86-0.92 (m, 3H).

後処理

  1. temperatureThe reaction mixture was heated to 50° C.
  2. stirringwith stirring for 3 h
  3. temperatureAfter cooling to RT
  4. concentrationthe mixture was concentrated
  5. custompurified by MPLC (0-100% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-00e7017c50c64c91a0ae0a1720295fa3
出典データセット
uspto-grants-2013_08
特許番号
US08513220B2

関連ノート

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