Hydrochloric Acid → HCID 59671361, compound

HRID 1747635Notes

Reaction equation

HRID 1747635 reaction equation
[S:1](=[O:34])(=[O:33])([O:3][CH2:4][C@@H:5]1[C@@H:12]2[C@@H:8]([O:9]C(C)(C)[O:11]2)[C@H:7]([N:15]([C:17]2[CH:22]=[C:21]([NH:23][C@@H:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:26][CH2:25]3)[N:20]=[CH:19][N:18]=2)[CH3:16])[CH2:6]1)[NH2:2].Cl>CO>[S:1](=[O:34])(=[O:33])([O:3][CH2:4][C@H:5]1[CH2:6][C@@H:7]([N:15]([C:17]2[CH:22]=[C:21]([NH:23][C@@H:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:26][CH2:25]3)[N:20]=[CH:19][N:18]=2)[CH3:16])[C@H:8]([OH:9])[C@@H:12]1[OH:11])[NH2:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86663354HCID 86663354, compound

Product 1

HCID 59671361HCID 59671361, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of {(3aR,4R,6R,6aS)-6-[{6-[(1S)-2,3-dihydro-1H-inden-1-ylamino]pyrimidin-4-yl}(methyl)amino]-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl}methyl sulfamate (12.0 mg, 0.02 mmol) in methanol (3.00 mL) was added 1.00 M hydrochloric acid (0.10 mL), and the mixture was stirred for 8 h. After quenching by addition of saturated NaHCO3 solution, the resulting mixture was evaporated under vacuum. The residue was purified via silica gel column chromatography eluting with a gradient of 5 to 10% methanol in DCM to afford the title compound (7.80 mg, 71%). 1H-NMR (400 MHz, CD3OD) δ: 8.01 (s, 1H), 7.27-7.13 (m, 4H), 5.67 (s, 1H), 5.42-5.34 (m, 1H), 4.88-4.75 (m, 1H), 4.17 (d, 2H, J=5.6 Hz), 4.04 (dd, 1H, J=8.8, 6.1 Hz), 3.88 (dd, 1H, J=5.8, 4.1 Hz), 3.05-2.96 (m, 1H), 2.89 (s, 3H), 2.93-2.83 (m, 1H), 2.62-2.52 (m, 1H), 2.34-2.24 (m, 1H), 2.01 (dt, 1H, d=13.0, 8.3 Hz), 1.94-1.83 (m, 1H), 1.44 (ddd, 1H, J=13.0, 10.8, 9.1). LC/MS: Rt=5.79 min, ES+ 450.2 (AA Waters).

Workup

  1. customAfter quenching by addition of saturated NaHCO3 solution
  2. customthe resulting mixture was evaporated under vacuum
  3. customThe residue was purified via silica gel column chromatography
  4. washeluting with a gradient of 5 to 10% methanol in DCM

Sources & evidence

ORD record
ord-26c47a2c93184666be759ea3259983d2
Source dataset
uspto-grants-2015_10
Patent number
US09150525B2

Reaction notes

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