Hydrochloric Acid → 3-But-2-ynyl-4-oxo-3,4-dihydro-imidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid amide

HRID 2098301ノート

反応式

HRID 2098301 の反応式
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.Br[CH2:17][C:18]#[C:19]C.C1CCN2C(=NCCC2)CC1.Cl>C(#N)C>[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)[C:17]#[C:18][CH3:19]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27568621-Bromo-2-butyneHCID 441283003-(Hydroxymethyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

生成物 1

HCID 441285553-But-2-ynyl-4-oxo-3,4-dihydro-imidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid amide

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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 the 1-bromo-2-butyne (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) δ ppm: 8.84 (1H, s), 7.82 (1H, s), 7.70 (1H, s), 5.08 (2H, q, J=2.4 Hz), 1.84 (3H, t, J=2.4 Hz).

後処理

  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

出典と根拠

ORDレコード
ord-355e19cecc9a4d008317651409c70838
出典データセット
uspto-grants-2013_05
特許番号
US08450479B2

反応ノート

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