Acetic Acid → HCID 76901355, 화합물

HRID 880318노트

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HRID 880318 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 76901355HCID 76901355, 화합물수율 3.1%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
22 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b858b50c06664db4be82efbe7d3a42eb
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993555B2

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