Diisopropylethylamine → HCID 18928965, compound

HRID 1599532Notes

Reaction equation

HRID 1599532 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([OH:16])=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN([P+](ON1N=NC2C1=CC=CC=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.Cl.[NH2:48][CH:49]1[CH:54]2[CH2:55][CH2:56][N:51]([CH2:52][CH2:53]2)[CH2:50]1.C(N(CC)C(C)C)(C)C>CN(C=O)C.C([O-])(O)=O.[Na+]>[C:1]1([S:7]([NH:10][C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([NH:48][CH:49]2[CH:54]3[CH2:55][CH2:56][N:51]([CH2:52][CH2:53]3)[CH2:50]2)=[O:16])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 7922013-Benzenesulfonamidobenzoic acidHCID 184012826530-09-2

Product 1

HCID 18928965HCID 18928965, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

3-(Phenylsulfonyl)aminobenzoic acid as prepared in Example 9 (139 mg, 0.5 mmol), Castro's reagent (benzotriazole-1-yloxytris(dimethylaminophosphonium hexafluorophosphate) (221 mg, 0.5 mmol), 3-aminoquinuclidine hydrochloride (100 mg, 0.5 mmol) and N,N-diisopropylethylamine (0.5 mL) were dissolved in dry DMF (2 mL) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with saturated NaHCO3 and extracted with ethyl acetate (3×). The combined ethyl acetate was washed with brine and dried over Na2SO4. After evaporation, the residue was purified by silica gel chromatography using 86% methylene chloride and 14% methanol containing 0.25 mL of acetic acid to give 65 mg (34% yield). 1H-NMR (300 MHz; DMSO-d6): d 1.69-2.14 (m,5H), 3.07-3.35 (m,6H), 3.63 (t, 1H, J=12 Hz), 4.22 (m, 1H), 7.23-7.77 (m, 9H), 8.53 (d, 1H, J=6 Hz). Mass spectrum (MALDI-TOF) calcd. for C20H23N3 O3S: 386.2 (M+H), Found: 386.2.

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined ethyl acetate was washed with brine
  3. dry with materialdried over Na2SO4
  4. customAfter evaporation
  5. customthe residue was purified by silica gel chromatography
  6. customto give 65 mg (34% yield)

Sources & evidence

ORD record
ord-5f220da9ca9f442fa8db4de06dcca82d
Source dataset
uspto-grants-1998_04
Patent number
US05741819

Reaction notes

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