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

HRID 2377057ノート

反応式

HRID 2377057 の反応式
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

参加物

4

反応物 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 68452512HCID 68452512、化合物

生成物 1

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

実験手順

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).

後処理

  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.)

出典と根拠

ORDレコード
ord-c218b6a312d24ddf8dd48e40e579b42c
出典データセット
uspto-grants-2008_12
特許番号
US07468375B2

反応ノート

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