Diisopropylethylamine → HCID 11977992, compound

HRID 2241164Notes

Reaction equation

HRID 2241164 reaction equation
[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

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 81909843-(3-chloro-benzenesulfonylamino)-benzoic acidHCID 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

Product 1

HCID 11977992HCID 11977992, compoundYield 15.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-f62b3ec66f2c490c8309d37883c9d4e1
Source dataset
uspto-grants-2010_05
Patent number
US07723538B2

Reaction notes

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