Nicotinic Acid → 1-Benzothiazol-6-yl-4-ethyl-3-pyridin-3-yl-1,3-dihydro-imidazol-2-one

HRID 80223

反応式

HRID 80223 の反応式
C([N:3]([CH2:6]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:15])=CC=1.C(O)(=O)[C:26]1[CH:31]=[CH:30][CH:29]=[N:28][CH:27]=1.[S:34]1[C:38]2[CH:39]=[C:40]([NH:43][CH2:44][C:45](=O)[CH2:46][CH3:47])[CH:41]=[CH:42][C:37]=2[N:36]=[CH:35]1>C1(C)C=CC=CC=1.C(Cl)Cl.CO>[S:34]1[C:38]2[CH:39]=[C:40]([N:43]3[CH:44]=[C:45]([CH2:46][CH3:47])[N:3]([C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)[C:6]3=[O:15])[CH:41]=[CH:42][C:37]=2[N:36]=[CH:35]1

参加物

8

反応物 4

HCID 938Nicotinic AcidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 596361951-(Benzothiazol-6-ylamino)-butan-2-one

生成物 1

HCID 498725541-Benzothiazol-6-yl-4-ethyl-3-pyridin-3-yl-1,3-dihydro-imidazol-2-one収率 1.5%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

実験手順

Triethylamine (0.2 mL, 1.219 mmol) and DPPA (0.3 mL, 1.219 mmol) were added to a solution of nicotinic acid (150 mg, 1.219 mmol) in toluene (12 mL) under nitrogen atmosphere and stirred at room temperature for 1.5 hours. The reaction mixture was allowed to reflux at 70° C. for 1.5 hours. The reaction was monitored by TLC (5% MeOH in DCM). This was followed by the addition of 1-(benzothiazol-6-ylamino)-butan-2-one (I-168a: 241 mg, 1.097 mmol) at room temperature. The resulting reaction mass was heated at 100° C. overnight. The reaction mixture was cooled to room temperature, concentrated under reduced pressure and the crude residue was partitioned between water and DCM. The organic layer was washed with water, brine solution, dried over Na2S4 and concentrated to afford the crude product. Purification by column chromatography on silica gel (1.5% methanol in chloroform) followed by preparative HPLC afforded 5 mg of the product (1.5% yield).

後処理

  1. temperatureto reflux at 70° C. for 1.5 hours
  2. customThe resulting reaction mass
  3. temperaturewas heated at 100° C. overnight
  4. temperatureThe reaction mixture was cooled to room temperature
  5. concentrationconcentrated under reduced pressure
  6. customthe crude residue was partitioned between water and DCM
  7. washThe organic layer was washed with water, brine solution
  8. customdried over Na2S4
  9. concentrationconcentrated
  10. customto afford the crude product
  11. customPurification by column chromatography on silica gel (1.5% methanol in chloroform)

出典と根拠

ORDレコード
ord-2b6e72233fb24c69876eb5743e2adf60
出典データセット
uspto-grants-2014_09
特許番号
USRE045173E1

関連ノート

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