Trifluoroacetic acid → HCID 24968962, compound

HRID 222161Notes

Reaction equation

HRID 222161 reaction equation
C(OC(=O)[NH:7][S:8]([O:11][CH2:12][C@@H:13]1[CH2:17][C@@H:16]([N:18]2[C:22]3[N:23]=[CH:24][N:25]=[C:26]([NH:27][C@H:28]4[C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[CH2:30][CH2:29]4)[C:21]=3[CH:20]=[CH:19]2)[CH2:15][C@@H:14]1[OH:37])(=[O:10])=[O:9])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[S:8](=[O:10])(=[O:9])([O:11][CH2:12][C@@H:13]1[CH2:17][C@@H:16]([N:18]2[C:22]3[N:23]=[CH:24][N:25]=[C:26]([NH:27][C@H:28]4[C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[CH2:30][CH2:29]4)[C:21]=3[CH:20]=[CH:19]2)[CH2:15][C@@H:14]1[OH:37])[NH2:7]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86614247tert-Butyl {[((1S,2S,4R)-4-{4-[(1R)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-2-hydroxycyclopentyl)methoxy]sulfonyl}carbamate

Product 1

HCID 24968962HCID 24968962, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl{[((1S,2S,4R)-4-{4-[(1R)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-2-hydroxycyclopentyl)methoxy]sulfonyl}carbamate (31.0 mg, 0.0570 mmol) was dissolved in DCM (0.803 mL) and trifluoroacetic acid (0.803 mL, 10.4 mmol) was added. The solution was stirred at rt for 15 min before being concentrated in vacuo. The residue was taken up in MeOH (5.00 mL), treated with solid sodium bicarbonate (300 mg) and stirred for 10 min. Filtration and silica gel chromatography eluting with a gradient of 0 to 10% MeOH in DCM afforded the title compound (7.20 mg, 58%). 1H NMR (400 MHz, CD3OD, δ): 8.17 (s, 1H), 7.27-7.14 (m, 5H), 6.64 (d, J=3.5 Hz, 1H), 5.86 (t, J=7.5 Hz, 1H), 5.49-5.42 (m, 1H), 4.51-4.48 (m, 1H), 4.38 (dd, J=7.5, 9.8 Hz, 1H), 4.21 (dd, J=7.3, 9.8 Hz, 1H), 3.10-3.03 (m, 1H), 2.97-2.88 (m, 1H), 2.86-2.76 (m, 1H), 2.68-2.60 (m, 1H), 2.37-2.21 (m, 3H), 2.08-1.97 (m, 2H) ppm. LC/MS: Rt=1.16 min, ES+ 444 (FA standard).

Workup

  1. concentrationbefore being concentrated in vacuo
  2. additiontreated with solid sodium bicarbonate (300 mg)
  3. stirringstirred for 10 min
  4. filtrationFiltration and silica gel chromatography
  5. washeluting with a gradient of 0 to 10% MeOH in DCM

Sources & evidence

ORD record
ord-6ae8b0436b6e4c09af2d34ed323b1599
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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