Dimethylamine → HCID 67411120, 화합물

HRID 1715581노트

반응식

HRID 1715581 반응식
CS(OS(C)(=O)=O)(=O)=O.[C:10]([C:14]1[CH:15]=[C:16]([NH:20][C:21]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[NH:31][C:32]2[CH:33]=[C:34]3[C:38](=[CH:39][CH:40]=2)[N:37]([CH2:41][CH2:42][CH2:43]O)[N:36]=[CH:35]3)=[O:22])[N:17]([CH3:19])[N:18]=1)([CH3:13])([CH3:12])[CH3:11].[CH:45]([N:48](C(C)C)[CH2:49]C)(C)C.CNC>C1COCC1>[C:10]([C:14]1[CH:15]=[C:16]([NH:20][C:21]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[NH:31][C:32]2[CH:40]=[C:39]3[C:38](=[CH:34][CH:33]=2)[N:37]([CH2:41][CH2:42][CH2:43][N:48]([CH3:49])[CH3:45])[N:36]=[CH:35]3)=[O:22])[N:17]([CH3:19])[N:18]=1)([CH3:11])([CH3:12])[CH3:13]

참가 물질

6

반응물 4

HCID 674Dimethylamine2회HCID 81531DiisopropylethylamineHCID 81560Methanesulfonic anhydrideHCID 67409607HCID 67409607, 화합물

생성물 1

HCID 67411120HCID 67411120, 화합물수율 43.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Methanesulfonic anhydride (12 mg, 0.070 mmol) was added to a solution of alcohol (7s) (24 mg, 0.050 mmol) and diisopropylethylamine (20 mg, 0.15 mmol) at room temperature. The solution was stirred for 1 hour. Dimethylamine (2.0 M in THF, 0.25 mL, 0.50 mmol) was added and the reaction was stirred overnight. Additional dimethylamine was added (2.0 M in THF, 0.25 mL, 0.50 mmol) and the reaction was stirred an additional 2 days. The mixture was then partitioned between CHCl3 and water. The aqueous phase was extracted once with CHCl3. The organic phases were combined, dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified on silica gel with 5% MeOH/CH2Cl2 containing 1% Et3N to provide the desired compound (8s-1) (11 mg, 43% yield) as a dark foam. 1H NMR (400 MHz, CDCl3) δ 7.81 (s, 1H), 7.42 (s, 1H), 7.35-7.33 (m, 2H), 7.19-7.11 (m, 4H), 6.80-6.75 (m, 2H), 5.94 (s, 1H), 5.55 (m, 1H), 4.43 (d, J=6.6 Hz, 2H), 4.38 (t, J=10.5 Hz, 2H), 3.57 (s, 3H), 2.24 (t, J=10.5 Hz, 2H), 2.19 (s, 6H), 2.08-2.01 (m, 2H), 1.24 (s, 9H); MS (ESI+) m/z 503 (M+H)+; HPLC (5 to 95%) 2.59 min.

후처리

  1. stirringthe reaction was stirred overnight
  2. stirringthe reaction was stirred an additional 2 days
  3. customThe mixture was then partitioned between CHCl3 and water
  4. extractionThe aqueous phase was extracted once with CHCl3
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified on silica gel with 5% MeOH/CH2Cl2 containing 1% Et3N

출처 및 근거

ORD 기록
ord-9d512d72500b47fab485ec8422ee1cde
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07799782B2

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