Diisopropylethylamine → 3-({1-[(5-Phenyl-1,3-oxazol-4-yl)carbonyl]pyrrolidin-2-yl}methyl)pyridine

HRID 1446300ノート

反応式

HRID 1446300 の反応式
[C:1]1([C:7]2[O:11][CH:10]=[N:9][C:8]=2[C:12]([OH:14])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:15]1[CH2:19][CH2:18][CH2:17][CH:16]1[CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=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>[C:1]1([C:7]2[O:11][CH:10]=[N:9][C:8]=2[C:12]([N:15]2[CH2:19][CH2:18][CH2:17][CH:16]2[CH2:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)=[O:14])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27762995-Phenyl-1,3-oxazole-4-carboxylic acidHCID 32638763-(2-Pyrrolidinylmethyl)pyridine

生成物 1

HCID 591701723-({1-[(5-Phenyl-1,3-oxazol-4-yl)carbonyl]pyrrolidin-2-yl}methyl)pyridine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

5-Phenyl-1,3-oxazole-4-carboxylic acid (40 mg, 0.211 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 C20H19N3O2: 333.1477, found 333.1484.

後処理

  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

出典と根拠

ORDレコード
ord-38be1efd17b849f497a1609bfaf62c92
出典データセット
uspto-grants-2010_02
特許番号
US07666888B2

反応ノート

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