2-(Methylamino)ethanol → Ammonium Acetate

HRID 522223

반응식

HRID 522223 반응식
[F:1][C:2]1[CH:32]=[C:6]2[CH:7]=[CH:8][C:9]3=[N:10][NH:11][C:12]4[C:13](=[CH:14][N:15]([CH3:31])[CH2:16][C:17]=4[C:18]4[CH2:25][CH:24]5[N:26]([CH2:27][C:28]([OH:30])=[O:29])[CH:20]([CH2:21][CH2:22][CH2:23]5)[CH:19]=4)[C:4](=[C:5]23)[CH:3]=1.[CH3:33][NH:34][CH2:35][CH2:36][OH:37].CN(C(N(C)C)=[N+]1C2C(=NC=CC=2)N=N1)C.C(N(CC)CC)C>CN(C)C=O>[C:28]([O-:30])(=[O:29])[CH3:27].[NH4+:10].[F:1][C:2]1[CH:32]=[C:6]2[CH:7]=[CH:8][C:9]3=[N:10][NH:11][C:12]4[C:13](=[CH:14][N:15]([CH3:31])[CH2:16][C:17]=4[C:18]4[CH2:25][CH:24]5[N:26]([CH2:27][C:28]([N:34]([CH2:35][CH2:36][OH:37])[CH3:33])=[O:29])[CH:20]([CH2:21][CH2:22][CH2:23]5)[CH:19]=4)[C:4](=[C:5]23)[CH:3]=1

참가 물질

7

반응물 4

HCID 80162-(Methylamino)ethanolHCID 8471TriethylamineHCID 118274210[3-(10-fluoro-7-methyl-6,7-dihydro-4H-3,4,7-triazadibenzo[cd,f]azulen-5-yl)-9-azabicyclo[3.3.1]non-2-en-9-yl]acetic acidHCID 178484285HCID 178484285, 화합물

생성물 2

HCID 517165Ammonium AcetateHCID 1182744102-[3-(10-fluoro-7-methyl-6,7-dihydro-4H-3,4,7-triazadibenzo[cd,f]azulen-5-yl)-9-azabicyclo[3.3.1]non-2-en-9-yl]-N-(2-hydroxyethyl)-N-methylacetamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of Example 103A (˜0.10 mmol), 2-(methylamino)ethanol (15.02 mg, 0.200 mmol), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxidhexafluorophosphate (HATU) (45.6 mg, 0.120 mmol) and triethylamine (69.7 μl, 0.500 mmol) in N,N-dimethylformamide (1.5 mL) was stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo and the residue was purified by reverse-phase HPLC performed on a Phenomenex Luna C8 AXIA column (30×75 mm, 100 Å) using a gradient of 10% to 95% acetonitrile: 10 mM ammonium acetate in water to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ 1.40-1.83 (m, 6H), 2.26 (dd, J=18.3, 10.2 Hz, 1H), 2.76 (dd, J=16.7, 9.9 Hz, 1H), 2.83 (s, 2H), 2.87 (s, 3H), 3.12 (s, 1H), 3.14-3.63 (m, 8H), 4.00-4.23 (m, 2H), 5.73 (d, J=5.0 Hz, 1H), 7.03-7.45 (m, 3H), 7.72 (dd, J=10.5, 2.9 Hz, 1H), 8.24 (d, J=5.2 Hz, 1H). MS (ESI) m/e 490.2 (M+H)+.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by reverse-phase HPLC

출처 및 근거

ORD 기록
ord-830774fdfb7f4f1e96990d62d3489012
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328112B2

연결된 노트

불러오는 중…