Diisopropylethylamine → 3-({1-[(3-Methyl-5-phenylisoxazol-4-yl)carbonyl]pyrrolidin-2-yl}methyl)pyridine

HRID 1446299노트

반응식

HRID 1446299 반응식
[CH3:1][C:2]1[C:6]([C:7]([OH:9])=O)=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:4][N:3]=1.[NH:16]1[CH2:20][CH2:19][CH2:18][CH:17]1[CH2:21][C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH3:1][C:2]1[C:6]([C:7]([N:16]2[CH2:20][CH2:19][CH2:18][CH:17]2[CH2:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[O:9])=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:4][N:3]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27765143-Methyl-5-phenylisoxazole-4-carboxylic acidHCID 32638763-(2-Pyrrolidinylmethyl)pyridine

생성물 1

HCID 591702443-({1-[(3-Methyl-5-phenylisoxazol-4-yl)carbonyl]pyrrolidin-2-yl}methyl)pyridine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

3-Methyl-5-phenyl-4-isoxazolecarboxylic acid (40 mg, 0.197 mmol), 3-(pyrrolidin-2-ylmethyl)pyridine (50.5 mg, 0.215 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (86.2 mg, 0.268 mmol) and diisopropylethylamine (25.4 mg, 0.197 mmol) were mixed in dimethylformamide (1.0 mL) and stirred at room temperature. Solvent was evaporated in vacuo, and the residue was taken up in methanol (1 mL), filtered and purified by preparative chromatography. The combined fractions were partitioned between NaHCO3 (sat) and ethylacetate. The organic layer was washed with water and concentrated in vacuo to afford the title compound. HRMS (ESI, pos. ion) m/z calcd for C21H21N3O2: 347.1634, found 347.1642.

후처리

  1. customSolvent was evaporated in vacuo
  2. filtrationfiltered
  3. custompurified by preparative chromatography
  4. customThe combined fractions were partitioned between NaHCO3 (sat) and ethylacetate
  5. washThe organic layer was washed with water
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-95b6aeec88fd4f12ad0a50e3f22fc281
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07666888B2

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