Hydrochloric Acid → HCID 71666343, compound

HRID 928241Notes

Reaction equation

HRID 928241 reaction equation
CC1(C)[O:6][C@H:5]2[C@H:7]([NH:12][C:13]3[N:18]4[N:19]=[C:20]([C:22]5[C:31]6[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=6)[CH:25]=[CH:24][CH:23]=5)[CH:21]=[C:17]4[N:16]=[CH:15][CH:14]=3)[CH2:8][C@H:9]([CH2:10][OH:11])[C@H:4]2[O:3]1.Cl[S:34]([NH2:37])(=[O:36])=[O:35].Cl.O>CN(C)C=O>[S:34](=[O:36])(=[O:35])([O:3][CH2:4][C@H:9]1[CH2:8][C@@H:7]([NH:12][C:13]2[N:18]3[N:19]=[C:20]([C:22]4[C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[CH:25]=[CH:24][CH:23]=4)[CH:21]=[C:17]3[N:16]=[CH:15][CH:14]=2)[C@H:5]([OH:6])[C@@H:10]1[OH:11])[NH2:37]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 24499Chlorosulfamic acidHCID 86692831HCID 86692831, compound

Product 1

HCID 71666343HCID 71666343, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a vial charged with (s.e.)-((3aR,4R,6R,6aS)-2,2-dimethyl-6-{[2-(1-naphthyl)pyrazolo[1,5-a]pyrimidin-7-yl]amino}tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methanol (1.76 g, 4.09 mmol) in N,N-dimethylformamide (7.20 mL) is added chlorosulfonamide (1.42 g, 12.3 mmol; obtained by the method described in J. Am. Chem. Soc. 2005, 127, 15391). After 1 hr, the reaction is quenched with methanol (5 mL). 6.0 M hydrochloric acid in water (3.41 mL, 20.4 mmol) is added and the mixture is stirred for 1 hr. Solvent is removed in vacuo and the crude material is purified by preparative HPLC to provide (s.e.)-((1R,2R,3S,4R)-2,3-dihydroxy-4-{[2-(1-naphthyl)pyrazolo[1,5-a]pyrimidin-7-yl]amino}cyclopentyl)methyl sulfamate. LCMS: (AA) M+1 470; 1H NMR (400 MHz, MeOD) δ 8.48-8.40 (m, 1H), 8.19 (d, J=5.5 Hz, 1H), 7.99-7.90 (m, 2H), 7.81-7.75 (m, 1H), 7.60-7.47 (m, 3H), 6.69 (s, 1H), 6.37 (d, J=5.6 Hz, 1H), 4.24-4.06 (m, 3H), 4.04-3.99 (m, 1H), 3.96-3.89 (m, 1H), 2.55-2.45 (m, 1H), 2.45-2.35 (m, 1H), 1.60-1.48 (m, 1H).

Workup

  1. customobtained by the method
  2. customthe reaction is quenched with methanol (5 mL)
  3. customSolvent is removed in vacuo
  4. customthe crude material is purified by preparative HPLC

Sources & evidence

ORD record
ord-fdf18b95d46147ae872708a87852b337
Source dataset
uspto-grants-2016_03
Patent number
US09290500B2

Reaction notes

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