Acetic Acid → HCID 76901355、化合物

HRID 880318ノート

反応式

HRID 880318 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[C:5]([NH:7][CH2:8][CH:9]([OH:21])[CH2:10][N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12]1)=[O:6].[CH3:25][C:26]1([CH3:33])[CH2:31][C:30](=O)[CH2:29][CH2:28][O:27]1.CC(O)=O.[BH3-]C#N.[Na+]>CO>[CH2:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:19][CH2:20][N:11]1[CH2:10][CH:9]([OH:21])[CH2:8][NH:7][C:5](=[O:6])[C:4]1[CH:22]=[CH:23][CH:24]=[C:2]([NH:1][CH:30]2[CH2:29][CH2:28][O:27][C:26]([CH3:33])([CH3:25])[CH2:31]2)[CH:3]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 17381592,2-Dimethyltetrahydropyran-4-oneHCID 5003444Sodium cyanoborohydrideHCID 902415853-amino-N-(3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)benzamide

生成物 1

HCID 76901355HCID 76901355、化合物収率 3.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
22 °C

実験手順

A solution of 3-amino-N-(3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)benzamide (130 mg, 0.4 mmol), 2,2-dimethyldihydro-2H-pyran-4(3H)-one (52 mg, 0.4 mmol) and AcOH (0.1 mL) in MeOH (10 mL). The mixture was stirred at 22° C. for 12 h, then NaBH3CN (76 mg, 1.2 mmol) was added and the resulting mixture was stirred at 22° C. for 2 h. The reaction mixture was concentrated and quenched with water. The aqueous mixture was extracted with DCM, the combined organic layers were concentrated and the residue was purified by prep-HPLC to give the title compound (5.5 mg, Yield 3.1%). 1H NMR (CD3OD, 400 MHz): δ 8.42 (brs, 1H) 7.00-7.33 (m, 7H) 6.84 (d, J=7.8 Hz, 1H) 4.21-4.41 (m, 3H) 3.40-3.92 (m, 8H) 3.11-3.20 (m, 3H) 1.91-2.07 (m, 2H) 1.18-1.44 (m, 8H). LCMS (m/z): 438.3 (M+1).

後処理

  1. stirringthe resulting mixture was stirred at 22° C. for 2 h
  2. concentrationThe reaction mixture was concentrated
  3. customquenched with water
  4. extractionThe aqueous mixture was extracted with DCM
  5. concentrationthe combined organic layers were concentrated
  6. customthe residue was purified by prep-HPLC

出典と根拠

ORDレコード
ord-b858b50c06664db4be82efbe7d3a42eb
出典データセット
uspto-grants-2015_03
特許番号
US08993555B2

反応ノート

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