Triethylsilane → (S)-1-(2-methoxy-1-phenylethyl)-3-(3-methoxy-1H-pyrazolo[4,3-c]pyridin-6-yl)urea

HRID 588179Notes

Reaction equation

HRID 588179 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]([NH:11][C:12]([NH:14][C:15]1[N:20]=[CH:19][C:18]2[C:21]([O:43][CH3:44])=[N:22][N:23](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:17]=2[CH:16]=1)=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C([SiH](CC)CC)C.C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O>[CH3:1][O:2][CH2:3][C@@H:4]([NH:11][C:12]([NH:14][C:15]1[N:20]=[CH:19][C:18]2[C:21]([O:43][CH3:44])=[N:22][NH:23][C:17]=2[CH:16]=1)=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 118272566(S)-1-(2-methoxy-1-phenylethyl)-3-(3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)urea

Product 1

HCID 118271892(S)-1-(2-methoxy-1-phenylethyl)-3-(3-methoxy-1H-pyrazolo[4,3-c]pyridin-6-yl)urea

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(S)-1-(2-Methoxy-1-phenylethyl)-3-(3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)urea (143 mg, 0.245 mmol) and triethylsilane (0.060 mL, 0.376 mmol) were stirred in TFA (2.5 mL) at room temperature for 30 min. Saturated NaHCO3 was added and the products extracted into EtOAc (×2). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification of the residue by flash chromatography (0-10% MeOH-EtOAc) gave (S)-1-(2-methoxy-1-phenylethyl)-3-(3-methoxy-1H-pyrazolo[4,3-c]pyridin-6-yl)urea. MS ESI calc'd. For C12H19N5O3 [M+1]+ 342. found 342. 1H NMR (500 MHz, DMSO-d6) δ 11.98 (s, 1H), 9.08 (s, 1H), 8.55 (s, 1H), 7.96 (br s, 1H), 7.48 (s, 1H), 7.34-7.30 (m, 4H), 7.25-7.21 (m, 1H), 4.98-4.93 (m, 1H), 3.96 (s, 3H), 3.55 (d, J=5.5 Hz, 2H), 3.25 (s, 3H).

Workup

  1. extractionthe products extracted into EtOAc (×2)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by flash chromatography (0-10% MeOH-EtOAc)

Sources & evidence

ORD record
ord-7ca1f077bb944b69985e94420194e52a
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

Loading…