Dimethylamine → 5-(N,N-dimethylaminocarbonyl)-2-methoxyphenylboronic acid

HRID 1478240노트

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HRID 1478240 반응식
[B:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:7](O)=[O:8])([OH:3])[OH:2].[CH3:15][NH:16][CH3:17].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[CH3:15][N:16]([CH3:17])[C:7]([C:6]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:4]([B:1]([OH:3])[OH:2])[CH:5]=1)=[O:8]

참가 물질

6

반응물 4

HCID 674DimethylamineHCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 426145415-Carboxy-2-methoxybenzeneboronic acid

생성물 1

HCID 575560785-(N,N-dimethylaminocarbonyl)-2-methoxyphenylboronic acid수율 45.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 700 mg (3.57 mmol) 3-borono-4-methoxybenzoic acid in 23 ml DMF, 3.6 ml (7.14 mmol) dimethylamine, 1.5 g (3.93 mmol) HATU and 1.57 ml (14.29 mmol) NMM were added and stirred at RT for 2 hours. The reaction mixture was extracted with EtOAc and water. The organic phase was dried over Na2SO4, filtered and evaporated. The residue was purified by preparative HPLC (Prep. HPLC method 1, gradient: 15-30% in 16 minutes). The fractions containing product were combined and extracted twice with EtOAc. The combined organic phases were dried over Na2SO4, filtered and evaporated to afford 361 mg (1.619 mmol, 45.3% yield) of the title compound as a colorless solid. LCMS: (M+H)=224; tR=0.54 min (LC-MS 4). 1H-NMR (d6-DMSO, 400 MHz) δ ppm 7.56 (m, 1H) 7.44 (dd, 1H) 6.99 (d, 1H) 3.81 (s, 3H) 2.93 (s, 6H).

후처리

  1. extractionThe reaction mixture was extracted with EtOAc and water
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by preparative HPLC (Prep. HPLC method 1, gradient: 15-30% in 16 minutes)
  6. additionThe fractions containing product
  7. extractionextracted twice with EtOAc
  8. dry with materialThe combined organic phases were dried over Na2SO4
  9. filtrationfiltered
  10. customevaporated

출처 및 근거

ORD 기록
ord-4c438aa47c594e108e8b5422e3718a58
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403827B2

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