Trifluoroacetic acid → [(1R,2S,4R)-4-({6-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]pyrimidin-4-yl}-amino)-2-hydroxycyclopentyl]methyl sulfamate

HRID 1397524Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1397524
[C@@H:1]1([NH:10][C:11]2[N:16]=[CH:15][N:14]=[C:13]([NH:17][C@@H:18]3[CH2:22][C@H:21]([CH2:23][O:24][S:25]([NH:28]C(=O)OC(C)(C)C)(=[O:27])=[O:26])[C@@H:20]([OH:36])[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.FC(F)(F)C(O)=O>C(Cl)Cl>[S:25](=[O:27])(=[O:26])([O:24][CH2:23][C@H:21]1[CH2:22][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][C@@H:20]1[OH:36])[NH2:28]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86618704tert-butyl ({[(1R,2S,4R)-4-({6-[(1S)-2,3-dihydro-1H-inden-1-ylamino]pyrimidin-4-yl}amino)-2-hydroxycyclopentyl]methoxy}sulfonyl)carbamate

Produkt 1

HCID 24829705[(1R,2S,4R)-4-({6-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]pyrimidin-4-yl}-amino)-2-hydroxycyclopentyl]methyl sulfamateAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl ({[(1R,2S,4R)-4-({6-[(1S)-2,3-dihydro-1H-inden-1-ylamino]pyrimidin-4-yl}amino)-2-hydroxycyclopentyl]methoxy}sulfonyl)carbamate (50.0 mg, 0.0962 mmol) in DCM (2.00 mL) was added trifluoroacetic acid (0.500 mL, 6.49 mmol), and the mixture was stirred for 30 min. The mixture was concentrated in vacuo and the residue was purified via silica gel chromatography eluting with 10% MeOH in DCM, and the product was dissolved in MeOH and treated with solid NaHCO3. The suspension was filtered and the filtrate was purified via silica gel chromatography eluting with 10% MeOH/DCM to afford the title compound as an amorphous solid (12.0 mg, 30%). 1H NMR (CD3OD, 400 MHz) δ: 7.94 (s, 1H), 7.29-7.12 (m, 4H), 5.53 (s, 1H), 5.32 (bs, 1H), 4.23-4.08 (m, 4H), 3.06-2.96 (m, 1H), 2.93-2.82 (m, 1H), 2.61-2.50 (m, 1H), 2.45-2.34 (m, 1H), 2.26-2.15 (m, 1H), 2.08-1.98 (m, 1H), 1.95-1.78 (m, 2H), 1.37-1.25 (m, 2H) ppm. LC/MS: Rt=1.29 min, ES+ 420. (AA standard).

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified via silica gel chromatography
  3. washeluting with 10% MeOH in DCM
  4. dissolutionthe product was dissolved in MeOH
  5. additiontreated with solid NaHCO3
  6. filtrationThe suspension was filtered
  7. customthe filtrate was purified via silica gel chromatography
  8. washeluting with 10% MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-07b5599b5fca4db69d3e37e912c7788a
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901136B2

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