Chlorosulfamic acid → HCID 178514805, compound

HRID 1677944Notes

Reaction equation

HRID 1677944 reaction equation
[C:1]1([C:11]2[NH:12][C:13]3[C:18]([N:19]=2)=[C:17]([O:20][C@H:21]2[CH2:25][CH2:24][C@H:23]([CH2:26][OH:27])[CH2:22]2)[N:16]=[CH:15][N:14]=3)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl[S:29]([NH2:32])(=[O:31])=[O:30]>CC(N(C)C)=O.CC#N>[S:29](=[O:31])(=[O:30])([O:27][CH2:26][C@H:23]1[CH2:24][CH2:25][C@H:21]([O:20][C:17]2[N:16]=[CH:15][N:14]=[C:13]3[C:18]=2[N:19]=[C:11]([C:1]2[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=2)[NH:12]3)[CH2:22]1)[NH2:32]

Participants

5

Reactant 2

HCID 24499Chlorosulfamic acidHCID 178520987HCID 178520987, compound

Product 1

HCID 178514805HCID 178514805, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ((1S,3S)-3-{[8-(1-naphthyl)-9H-purin-6-yl]oxy}cyclopentyl)-methanol (66.1 mg, 0.000183 mol) in DMA (8.12 mL) at 0° C. was added chlorosulfonamide (106 mg, 0.00091.7 mol) in CH3CN (2.0 mL). The reaction was stirred at 0° C. for 10 mins, then 23° C. for 3 hours. The reaction was quenched with water and extracted with EtOAc (3×). The combined organics were washed with water (2×), dried (Na2SO4), filtered, and concentrated. The residue was purified by flash chromatography (0 to 6% MeOH/CH2Cl2) to obtain 56.3 mg (70%) of the title compound as a white solid. 1H NMR (CD3OD, 400 MHz) δ: 8.52-8.48 (m, 2H), 8.10-8.07 (m, 111, 8.01-7.98 (m, 1H), 7.90-7.87 (m, 1H), 7.65-7.57 (m, 3H), 5.89-5.85 (m, 1H), 4.12-4.07 (m, 2H), 2.75-2.66 (m, 1H), 2.30-2.21 (m, 2H), 2.16-2.01 (m, 2H), 1.93-1.85 (m, 1H), 1.62-1.53 (m, 1H) ppm. LC/MS: Rt=1.38 min, ES+ 442 (FA standard).

Workup

  1. wait23° C. for 3 hours
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc (3×)
  4. washThe combined organics were washed with water (2×)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (0 to 6% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-586b6c338f6a42bc8040fb65992c9e1d
Source dataset
uspto-grants-2011_08
Patent number
US08008307B2

Reaction notes

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