Acetonitrile → [(3aR,4R,6R,6aS)-6-({6-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]pyrimidin-4-yl}-amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methyl sulfamate

HRID 447573Notes

Reaction equation

HRID 447573 reaction equation
[C@@H:1]1([NH:10][C:11]2[N:16]=[CH:15][N:14]=[C:13]([NH:17][C@H:18]3[C@@H:22]4[O:23][C:24]([CH3:27])([CH3:26])[O:25][C@@H:21]4[C@@H:20]([CH2:28][OH:29])[CH2:19]3)[CH:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.CCN(CC)CC.Cl[S:38]([NH2:41])(=[O:40])=[O:39].C(#N)C>C(Cl)Cl>[S:38](=[O:40])(=[O:39])([O:29][CH2:28][C@@H:20]1[C@@H:21]2[C@@H:22]([O:23][C:24]([CH3:26])([CH3:27])[O:25]2)[C@H:18]([NH:17][C:13]2[CH:12]=[C:11]([NH:10][C@@H:1]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH2:3][CH2:2]3)[N:16]=[CH:15][N:14]=2)[CH2:19]1)[NH2:41]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 24499Chlorosulfamic acidHCID 66797856[(3aR,4R,6R,6aS)-6-({6-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]pyrimidin-4-yl}-amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methanol

Product 1

HCID 86618703[(3aR,4R,6R,6aS)-6-({6-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]pyrimidin-4-yl}-amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methyl sulfamateYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of [(3aR,4R,6R,6aS)-6-({6-[(1S)-2,3-dihydro-1H-inden-1-ylamino]pyrimidin-4-yl}amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-methanol (100. mg, 0.252 mmol) and Et3N (0.0527 mL, 0.378 mmol) in DCM (2.50 mL) was added dropwise a 2.00 M solution of chlorosulfonamide in ACN (0.190 mL, 0.380 mmol) at 0° C. and the mixture was stirred for 2 h. The reaction was diluted with DCM, quenched with H2O and the organic layer was separated, then concentrated in vacuo. The residue was purified via silica gel chromatography eluting with a gradient of 0 to 10% MeOH in DCM to afford the title compound (65.0 mg, 54%). LC/MS: Rt=1.58 min, ES+ 476 (AA standard).

Workup

  1. customquenched with H2O
  2. customthe organic layer was separated
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified via silica gel chromatography
  5. washeluting with a gradient of 0 to 10% MeOH in DCM

Sources & evidence

ORD record
ord-f7c35babe6c548f7a62aa1fc67beadb7
Source dataset
uspto-grants-2013_07
Patent number
US08481550B2

Reaction notes

Loading…