Methanol → Methyl (6S)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylate--hydrogen chloride (1/2)

HRID 2377057노트

반응식

HRID 2377057 반응식
S(Cl)([Cl:3])=O.[ClH:5].Cl.[N:7]1[C:15]2[CH2:14][C@@H:13]([C:16]([OH:18])=[O:17])[NH:12][CH2:11][C:10]=2[NH:9][CH:8]=1.[CH3:19]O>>[ClH:3].[ClH:5].[N:7]1[C:15]2[CH2:14][C@@H:13]([C:16]([O:18][CH3:19])=[O:17])[NH:12][CH2:11][C:10]=2[NH:9][CH:8]=1

참가 물질

4

반응물 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 68452512HCID 68452512, 화합물

생성물 1

HCID 14403671Methyl (6S)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylate--hydrogen chloride (1/2)수율 100%

실험 절차

Thionylchloride (200 mL, 2.74 mol, 3.0 mol eqv.) was added dropwise to methanol (3.5 L), which was cooled to 0-5° C. (6S)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid dihydrochloride (210.0 g, 0.87 mol) was added The suspension was allowed to warm up to room temperature, and refluxed for 3.5 h. After cooling to room temperature, the solvent was removed under reduced pressure. The white residue was suspended in ether (3 L). The solid was filtered and washed with ether. After drying in a vacuum oven (40° C.), the title compound was obtained (225.0 g, 100% yield, 95% pure). 1H NMR (DMSO-d6): δ ppm 12.65 (br s, 2H), 9.04 (s, 1H), 4.71 (m, 1H), 4.33 (t, J=16.2 Hz, 2H), 3.81 (s, 3H), 3.10-3.33 (m, 2H), LCMS: Rt=0.61 min and M+1=182.1 u/e (M+1 of free base).

후처리

  1. additionwas added The suspension
  2. temperaturerefluxed for 3.5 h
  3. temperatureAfter cooling to room temperature
  4. customthe solvent was removed under reduced pressure
  5. filtrationThe solid was filtered
  6. washwashed with ether
  7. customAfter drying in a vacuum oven (40° C.)

출처 및 근거

ORD 기록
ord-c218b6a312d24ddf8dd48e40e579b42c
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07468375B2

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