Diisopropylamine → HCID 57980847, compound

HRID 1867989Notes

Reaction equation

HRID 1867989 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][S:12]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:22]1([C:27](O)=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(NC(C)C)(C)C>CN(C)C=O.C(OCC)(=O)C.O>[CH:22]1([C:27]([NH:1][C:2]2[S:3][C:4]3[CH:10]=[C:9]([O:11][S:12]([C:15]4[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=4)(=[O:13])=[O:14])[CH:8]=[CH:7][C:5]=3[N:6]=2)=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 18840Cyclopentanecarboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 579808144-Fluorobenzenesulfonic acid 2-aminobenzothiazol-6-yl ester2×

Product 1

HCID 57980847HCID 57980847, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-fluorobenzenesulfonic acid 2-aminobenzothiazol-6-yl ester (intermediate 16) (101.2 mg, 0.312 mmol), cyclopentanecarboxylic acid (53.4 mg, 0.936 mmol), HBTU (355 mg, 0.936 mmol) and N,N-diisopropyl-amine (326 μl, 1.872 mmol) in 5 ml of dimethylformamide in a test tube, equipped with a magnetic bar, is stirred for 20 hours at room temperature. 100 ml of water are added and the reaction medium is extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and evaporated. The residue obtained is taken up in ethyl acetate and purified on a Varian flash cartridge containing 5 g of silica of porosity 15-35μ, with a mixture of 1% methanol in dichloromethane. After evaporating off the solvent, 90 mg of 4-fluorobenzenesulfonic acid 2-(cyclopentane carbonylamino)benzothiazol-6-yl ester are obtained (yellow oil) in a yield of 68%. LC/MS (method A1): [M+H]+: 421.13, retention time: 4.05 min.

Workup

  1. extractionthe reaction medium is extracted with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customevaporated
  4. customThe residue obtained
  5. custompurified on a Varian flash cartridge
  6. additioncontaining 5 g of silica of porosity 15-35μ
  7. additionwith a mixture of 1% methanol in dichloromethane
  8. customAfter evaporating off the solvent, 90 mg of 4-fluorobenzenesulfonic acid 2-(cyclopentane carbonylamino)benzothiazol-6-yl ester
  9. customare obtained (yellow oil) in a yield of 68%

Sources & evidence

ORD record
ord-a2bdc4a4de0940bc988018ae8ccffd88
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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