Methoxyacetonitrile → HCID 178494690, 화합물

HRID 1056836

반응식

HRID 1056836 반응식
C(O[C:4]([C:6]1[C:7]2[CH2:15][CH2:14][CH2:13][CH2:12][C:8]=2[S:9][C:10]=1[NH2:11])=[O:5])C.[CH3:16][O:17][CH2:18][C:19]#[N:20]>O1CCOCC1.Cl>[CH3:16][O:17][CH2:18][C:19]1[N:20]=[C:4]([OH:5])[C:6]2[C:7]3[CH2:15][CH2:14][CH2:13][CH2:12][C:8]=3[S:9][C:10]=2[N:11]=1

참가 물질

5

반응물 2

HCID 74442MethoxyacetonitrileHCID 78262Ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate

생성물 1

HCID 178494690HCID 178494690, 화합물

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 312751,4-Dioxane용매

실험 절차

To a stirred mixture of 2-Amino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester (2.0 g, 0.0088 mol) and methoxyacetonitrile (1.3 ml, 0.0177 mol) in 1,4-dioxane (200 nml), dry HCl gas was purged for 30-45 minutes at 0-5° C. The reaction mixture was then warmed to room temperature and stirred for about 20 h under inert atmosphere. After completion of the reaction, the mixture was quenched with the addition of crushed ice (˜200 g). The aqueous layer was then extracted well with ethyl acetate (2×250 ml). Combined organic layers was washed with brine solution (100 ml) dried over anhydrous Na2SO4 and concentrated under vacuum to get crude 2-Methoxymethyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-ol as brown colored solid which was forwarded as such for the next step. Yield: (2 g, 90%); 1H NMR (400 MHz, DMSO) δ ppm=12.27 (s, 1H), 4.28 (s, 2H), 3.31 (s, 3H), 2.87-2.84 (m, 2H), 2.74-2.71 (m, 2H), 1.81-1.73 (m, 4H); LCMS: [M+H]=251.1.

후처리

  1. customwas purged for 30-45 minutes at 0-5° C
  2. customAfter completion of the reaction
  3. customthe mixture was quenched with the addition of crushed ice (˜200 g)
  4. extractionThe aqueous layer was then extracted well with ethyl acetate (2×250 ml)
  5. washCombined organic layers was washed with brine solution (100 ml)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-b17012cab3e54703acd5209bba286177
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09399647B2

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