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Diisopropylethylamine → HCID 11977992, 화합물

HRID 2241164
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HRID 2241164 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([OH:17])=O)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.C([O:23][C:24](=[O:33])[C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][C:26]=1[F:32])C.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([NH:31][C:28]2[CH:29]=[CH:30][C:25]([C:24]([OH:33])=[O:23])=[C:26]([F:32])[CH:27]=2)=[O:17])(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1
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참가 물질

8

반응물 4

HCID 81531DiisopropylethylamineHCID 8190984Amberlite IR 120 PlusHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10797532Ethyl 4-Amino-2-fluorobenzoate

생성물 1

HCID 11977992HCID 11977992, 화합물수율 15.6%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

A solution of 3-(3-chloro-benzenesulfonylamino)-benzoic acid (31.1 mg, 0.10 mmol) in DMF (0.5 ml) was added to 4-amino-2-fluoro-benzoic acid ethyl ester (20.1 mg, 0.11 mmol). Diisopropyl-ethyl-amine (0.035 ml) was added, followed by a solution of HATU (57.0 mg, 0.15 mmol) in DMF (0.5 ml). The mixture was shaken at room temperature overnight, then diluted with ethyl acetate (4.0 ml) and water (2.0 ml). The organic phase was separated and evaporated. The residue was dissolved in ethanol (0.60 ml) and treated with 3N KOH (0.40 ml). The mixture was shaken at room temperature overnight, then acidified to pH 2 with 3N HCl. Purification by preparative HPLC (ZORBAX Eclipse XDB-C18, 21.2×50 mm, 5 μm, gradient acetonitrile/water+0.1% formic acid) yielded the title compound (7.0 mg, 15%) as a white solid, MS (ISP): m/e=447.0 (M−H).

후처리

  1. customThe organic phase was separated
  2. customevaporated
  3. dissolutionThe residue was dissolved in ethanol (0.60 ml)
  4. additiontreated with 3N KOH (0.40 ml)
  5. stirringThe mixture was shaken at room temperature overnight
  6. customPurification by preparative HPLC (ZORBAX Eclipse XDB-C18, 21.2×50 mm, 5 μm, gradient acetonitrile/water+0.1% formic acid)

출처 및 근거

ORD 기록
ord-f62b3ec66f2c490c8309d37883c9d4e1
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07723538B2

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