Hydrochloric Acid → 4-Oxo-3-(3-trimethylsilanyl-prop-2-ynyl)-3,4-dihydro-imidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid amide

HRID 2098302노트

반응식

HRID 2098302 반응식
O[CH2:2][N:3]1[C:8](=[O:9])[N:7]2[CH:10]=[N:11][C:12]([C:13]([NH2:15])=[O:14])=[C:6]2[N:5]=[N:4]1.BrC[C:18]#[C:19][Si:20]([CH3:23])([CH3:22])[CH3:21].C1CCN2C(=NCCC2)CC1.Cl>C(#N)C>[O:9]=[C:8]1[N:3]([CH2:2][C:18]#[C:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[N:4]=[N:5][C:6]2=[C:12]([C:13]([NH2:15])=[O:14])[N:11]=[CH:10][N:7]12

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 6425893-Bromo-1-(trimethylsilyl)-1-propyneHCID 441283003-(Hydroxymethyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

생성물 1

HCID 441285564-Oxo-3-(3-trimethylsilanyl-prop-2-ynyl)-3,4-dihydro-imidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid amide

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a cooled solution of 3-(Hydroxymethyl)-4-oxo-3,4-dihydroimidazo[5,1-][1,2,3,5]tetrazine-8-carboxamide (MM-001) (1 equiv) in acetonitrile (0.17 M concentration substrate in solvent) was added 3-bromo-1-(trimethylsilyl)-1-propyne (4 equivs) and DBU (1.4 equivs). The mixture was stirred at this temperature for 30 minutes whereupon it was acidified with 1 N HCl. The mixture was extracted with EtOAc (3×1 reaction volume). The combined organic extracts were combined, dried (MgSO4), filtered and concentrated in vacuo to give an oily residue which was then precipitated from Et2O and washed with further Et2O to give the title compound. 1H NMR (400 MHz, d6-DMSO) □ ppm: 8.87 (1H, s), 7.86 (1H, s), 7.72 (1H, s), 5.18 (2H, s), 0.16 (9H, s). LCMS: rt=3.24 min.; m/z: 313.4 (M+Na)+, 291.2 (MH)+, 151.4 (100).

후처리

  1. extractionThe mixture was extracted with EtOAc (3×1 reaction volume)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give an oily residue which
  6. customwas then precipitated from Et2O
  7. washwashed with further Et2O

출처 및 근거

ORD 기록
ord-bd5317afe5ca4ae785e9f2fb13f45362
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450479B2

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