Triethylamine → (3-(4-(6-Oxa-2-azaspiro[3.4]octan-2-ylmethyl)phenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

HRID 2359371노트

반응식

HRID 2359371 반응식
[C:1]1([C:7]2[O:11][C:10]([C:12]([N:14]3[CH2:17][CH:16]([O:18][C:19]4[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=4)[CH2:15]3)=[O:13])=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH2:28]1[C:31]2([CH2:35][CH2:34][O:33][CH2:32]2)[CH2:30][NH:29]1.C(N(CC)CC)C.[Na].C([O-])(O)=O.[Na+]>ClCCl>[CH2:28]1[C:31]2([CH2:35][CH2:34][O:33][CH2:32]2)[CH2:30][N:29]1[CH2:23][C:22]1[CH:21]=[CH:20][C:19]([O:18][CH:16]2[CH2:15][N:14]([C:12]([C:10]3[O:11][C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[N:8][N:9]=3)=[O:13])[CH2:17]2)=[CH:26][CH:25]=1

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 58043115HCID 58043115, 화합물HCID 717440076-Oxa-2-azaspiro(3.4)octane hydrochloride

생성물 1

HCID 71226400(3-(4-(6-Oxa-2-azaspiro[3.4]octan-2-ylmethyl)phenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-(1-(5-phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehyde (70 mg, 0.20 mmol) in dichloromethane (2 mL) was added 6-oxa-2-azaspiro[3.4]octane hydrochloride (56 mg, 0.37 mmol) and triethylamine (0.100 mL, 0.72 mmol). After stirring at ambient temperature for 30 minutes, sodium triacetoxyhydroborate (95 mg, 0.45 mmol) was added. Stirring was continued at ambient temperature overnight, after which NaHCO3 (aq, sat, 5 ml) was added. The phases were separated with the aid of a phase separator. The aqueous phase was extracted twice with dichloromethane and dried using a phase separator. The combined organic phases were concentrated in vacuo to afford a colourless residue weighing 92 mg.

후처리

  1. stirringStirring
  2. waitwas continued at ambient temperature overnight
  3. customThe phases were separated with the aid of a phase separator
  4. extractionThe aqueous phase was extracted twice with dichloromethane
  5. customdried
  6. concentrationThe combined organic phases were concentrated in vacuo
  7. customto afford a colourless residue

출처 및 근거

ORD 기록
ord-3ed8f0a8401f4f23b0a111465b767a4b
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08685958B2

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