Ammonia → 3-(8-Amino-1-iodoimidazo[1,5-a]pyrazin-3-yl)-1-methylcyclobutanol

HRID 1993173노트

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HRID 1993173 반응식
[NH3:1].Cl[C:3]1[C:4]2[N:5]([C:9]([CH:13]3[CH2:16][C:15]([CH3:18])([OH:17])[CH2:14]3)=[N:10][C:11]=2[I:12])[CH:6]=[CH:7][N:8]=1>C(O)(C)C.C1COCC1>[NH2:1][C:3]1[C:4]2[N:5]([C:9]([CH:13]3[CH2:16][C:15]([CH3:18])([OH:17])[CH2:14]3)=[N:10][C:11]=2[I:12])[CH:6]=[CH:7][N:8]=1

참가 물질

5

반응물 2

HCID 222AmmoniaHCID 533286203-(8-Chloro-1-iodoimidazo[1,5-a]pyrazin-3-yl)-1-methylcyclobutanol

생성물 1

HCID 533289773-(8-Amino-1-iodoimidazo[1,5-a]pyrazin-3-yl)-1-methylcyclobutanol

시약·촉매·용매 2

HCID 3776Isopropanol용매HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

A solution of 2M ammonia in isopropanol (80 mL) and THF (5 mL) was added to 3-(8-chloro-1-iodoimidazo[1,5-a]pyrazin-3-yl)-1-methylcyclobutanol (2.77 g, 7.62 mmol) in a Parr pressure reactor. The mixture was cooled to at −78° C. then ammonia gas was bubbled into the solution for 4-6 min. The reactor was sealed then heated at 110° C. for 15 h. The solvent was then removed in vacuo and the residue purified by chromatography over silica gel eluting with 7% MeOH in DCM to afford desired product. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.44 (s, 3 H), 2.32-2.51 (m, 4 H), 3.33-3.52 (m, 1 H), 6.61 (br.s., 2 H), 7.03 (d, J=5.05 Hz, 1 H) and 7.62 (d, J=5.05 Hz, 1 H).

후처리

  1. customammonia gas was bubbled into the solution for 4-6 min
  2. customThe reactor was sealed
  3. temperaturethen heated at 110° C. for 15 h
  4. customThe solvent was then removed in vacuo
  5. customthe residue purified by chromatography over silica gel eluting with 7% MeOH in DCM

출처 및 근거

ORD 기록
ord-340b849dc00346bf8456b11f53ba5afd
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07651687B2

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