Diisopropylethylamine → ethyl 4-(3-(2-((tert-butoxycarbonylamino)methyl) acrylamido)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

HRID 882140ノート

反応式

HRID 882140 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH:5]=[CH:6][CH:7]=1.[C:22]([O:26][C:27]([NH:29][CH2:30][C:31](=[CH2:35])[C:32](O)=[O:33])=[O:28])([CH3:25])([CH3:24])[CH3:23].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[C:22]([O:26][C:27]([NH:29][CH2:30][C:31](=[CH2:35])[C:32]([NH:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH:5]=[CH:6][CH:7]=1)=[O:33])=[O:28])([CH3:25])([CH3:24])[CH3:23]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71598790ethyl 4-(3-aminophenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylateHCID 896132672-({[(Tert-butoxy)carbonyl]amino}methyl)prop-2-enoic acid

生成物 1

HCID 89630003ethyl 4-(3-(2-((tert-butoxycarbonylamino)methyl) acrylamido)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of ethyl 4-(3-aminophenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (300 mg, 1.06 mmol), 2-((tert-butoxycarbonylamino)methyl)acrylic acid (321 mg, 1.60 mmol), HATU (606 mg, 1.59 mmol) and DIPEA (371 μL, 2.13 mmol) in DMF (5.0 mL) was stirred at room temperature for 3 hours. The resulting mixture was diluted with ethyl acetate (15 mL) and washed with saturated aqueous bicarbonate, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by reverse phase HPLC using an acetonitrile gradient in water with 0.1% TFA modifier to give ethyl 4-(3-(2-((tert-butoxycarbonylamino)methyl)acrylamido)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate. LRMS (ESI) calc'd for C24H28N5O5 [M+H]+: 466, found 466.

後処理

  1. washwashed with saturated aqueous bicarbonate, brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by reverse phase HPLC

出典と根拠

ORDレコード
ord-7b18c8fec0c54502badc6c6a514642a8
出典データセット
uspto-grants-2015_03
特許番号
US08993756B2

反応ノート

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