Triethylsilane → (R)-1-(3-ethyl-1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridin-7-yl)-3-(1-phenylethyl)urea

HRID 590849Notes

Reaction equation

HRID 590849 reaction equation
[CH2:1]([N:3]1[CH2:12][CH2:11][C:10]2[N:9]=[C:8]([NH:13][C:14]([NH:16][C@@H:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH3:18])=[O:15])[CH:7]=[C:6]3[N:25](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:26]=[C:4]1[C:5]=23)[CH3:2].C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[CH2:1]([N:3]1[CH2:12][CH2:11][C:10]2[N:9]=[C:8]([NH:13][C:14]([NH:16][C@@H:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH3:18])=[O:15])[CH:7]=[C:6]3[NH:25][N:26]=[C:4]1[C:5]=23)[CH3:2]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 118272227(R)-1-(3-ethyl-1-trityl-1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridin-7-yl)-3-(1-phenylethyl)urea

Product 1

HCID 73505439(R)-1-(3-ethyl-1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridin-7-yl)-3-(1-phenylethyl)urea

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(R)-1-(3-ethyl-1-trityl-1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridin-7-yl)-3-(1-phenylethyl)urea (27 mg, 0.045 mmol) was taken in TFA (0.1 mL) and stirred at room temperature for 30 minutes. To the reaction was added triethylsilane (21 uL, 0.128 mmol) and the mixture was stirred for 15 minutes at room temperature before it was heated at 80° C. for 30 minutes. The reaction mixture was concentrated, taken in DCM and washed with aqueous sodium bicarbonate, brine, dried with sodium sulfate and concentrated. Purification of the residue by flash column (0-15% MeOH-DCM) gave (R)-1-(3-ethyl-1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridin-7-yl)-3-(1-phenylethyl)urea. MS ESI calc'd. for C19H22N6O [M+H]+ 351. found 351. 1H NMR (ppm, 500 MHz, DMSO-d6) δ 7.32 (dd, J=3.4, 7.9, 4H), 7.24-7.14 (m, 1H), 6.40 (s, 1H), 4.90-4.79 (m, 1H), 4.02-3.89 (m, 2H), 3.40 (m, 2H), 3.01 (m, 2H), 1.40 (d, J=6.9, 3H), 1.24 (t, J=9.4, 3H).

Workup

  1. stirringthe mixture was stirred for 15 minutes at room temperature before it
  2. temperaturewas heated at 80° C. for 30 minutes
  3. concentrationThe reaction mixture was concentrated
  4. washwashed with aqueous sodium bicarbonate, brine
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. customPurification of the residue by flash column (0-15% MeOH-DCM)

Sources & evidence

ORD record
ord-e9666b4f9c3148c286842d07b0aefaae
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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