2-(Dimethylamino)ethanol → HCID 59540969, 화합물

HRID 1677544노트

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HRID 1677544 반응식
[CH3:1][C:2]1([CH3:40])[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[C:9]([C:17]3[N:18]=[C:19]4[C:25]([C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:24][N:23]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:20]4=[N:21][CH:22]=3)[CH:10]=[C:11]([O:13][CH2:14]OC)[CH:12]=2)[CH2:3]1.[CH3:41][N:42]([CH3:46])[CH2:43]CO.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:41][N:42]([CH3:46])[CH2:43][CH2:14][O:13][C:11]1[CH:10]=[C:9]([C:17]2[N:18]=[C:19]3[C:25]([C:26](=[O:31])[C:27]([CH3:28])([CH3:29])[CH3:30])=[CH:24][N:23]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:38])([CH3:37])[CH3:39])[C:20]3=[N:21][CH:22]=2)[CH:8]=[C:7]([N:4]2[CH2:5][CH2:6][C:2]([CH3:40])([CH3:1])[CH2:3]2)[CH:12]=1

참가 물질

6

반응물 4

HCID 79022-(Dimethylamino)ethanol3회HCID 11776Triphenylphosphine2회HCID 75555Diisopropyl diazene-1,2-dicarboxylate2회HCID 59540909HCID 59540909, 화합물

생성물 1

HCID 59540969HCID 59540969, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A flask was charged with 1-[2-[3-(3,3-dimethyl-pyrrolidin-1-yl)-5-methoxymethoxy-phenyl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (90 mg, 0.17 mmol), 2-dimethylamino-ethanol (reagent A, 0.04 ml, 0.34 mmol) and triphenylphosphine (reagent B, 90 mg, 0.34 mmol). THF (2 ml) was added under nitrogen atmosphere. Diisopropyl azodicarboxylate (reagent C, 0.07 ml, 0.34 mmol) was added via syringe and the material was stirred. After 1 hour a further 2 equivalents each of reagents A, B and C were added. The mixture was stirred overnight. The crude was loaded onto 2 preparative TLC plates eluting with 3% MeOH in dichloromethane. The plates were dried and re-developed with the solvent system. This process was repeated once more and then product band was collected providing 1-[2-[3-(2-dimethylamino-ethoxy)-5-(3,3-dimethyl-pyrrolidin-1-yl)-phenyl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one, 56 mg, as a golden yellow viscous oil.

후처리

  1. stirringThe mixture was stirred overnight
  2. washeluting with 3% MeOH in dichloromethane
  3. customThe plates were dried and re-developed with the solvent system
  4. customproduct band was collected

출처 및 근거

ORD 기록
ord-f72be0105a0a465a858280b716071f22
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008298B2

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