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Diisopropylethylamine → Ethyl 2-(4-(4-(tert-butoxycarbonylamino)phenylthio)-3-(7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)benzamido)-2-phenylpropanoate

HRID 605410
ノート
印刷プレビュー

反応式

HRID 605410 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][C:17]=2[NH:25][C:26]2[C:27]3[CH:35]=[CH:34][C:33]([CH:36]([CH3:38])[CH3:37])=[N:32][C:28]=3[N:29]=[CH:30][N:31]=2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[NH2:61][C:62]([C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)([CH3:68])[C:63]([O:65][CH2:66][CH3:67])=[O:64].C(N(CC)C(C)C)(C)C>CS(C)=O.O>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([S:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([NH:61][C:62]([C:69]3[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=3)([CH3:68])[C:63]([O:65][CH2:66][CH3:67])=[O:64])=[O:21])=[CH:18][C:17]=2[NH:25][C:26]2[C:27]3[CH:35]=[CH:34][C:33]([CH:36]([CH3:38])[CH3:37])=[N:32][C:28]=3[N:29]=[CH:30][N:31]=2)=[CH:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 3571202Ethyl 2-amino-2-phenylpropanoateHCID 593768924-(4-tert-Butoxycarbonylamino-phenylsulfanyl)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-benzoic acid

生成物 1

HCID 67040905
Ethyl 2-(4-(4-(tert-butoxycarbonylamino)phenylthio)-3-(7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)benzamido)-2-phenylpropanoate
収率 78%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

The product of Example 385E (90 mg, 0.17 mmol), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate [TBTU] (60 mg, 0.19 mmol) and ethyl 2-amino-2-phenylpropanoate (39 mg., 0.20 mmol) in DMSO (0.9 mL) was reacted with N,N-diisopropylethylamine (0.060 mL, 0.34 mmol) dropwise at room temperature then stirred at room temperature for 18 hours under N2. The mixture was poured into water (10 mL) with stirring. The resulting precipitate was extracted with ethyl acetate (50 mL) and the organic layer was washed with water (3×), saturated aqueous NaHCO3, then brine, dried over MgSO4, and concentrated. The residue was purified by silica gel chromatography (ethyl acetate:chloroform 4:1) to give the title compound as a pale yellow amorphous solid (93 mg, 78%).

後処理

  1. stirringwith stirring
  2. extractionThe resulting precipitate was extracted with ethyl acetate (50 mL)
  3. washthe organic layer was washed with water (3×), saturated aqueous NaHCO3
  4. dry with materialbrine, dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (ethyl acetate:chloroform 4:1)

出典と根拠

ORDレコード
ord-f82061a7bcee4df588651382d9c7f1c7
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07910595B2

反応ノート

読み込み中…

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