Triethylsilane → HCID 73505440, compound

HRID 590852Notes

Reaction equation

HRID 590852 reaction equation
[CH:1]([N:4]1[CH2:13][CH2:12][C:11]2[N:10]=[C:9]([NH:14][C:15]([NH:17][C@@H:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH3:19])=[O:16])[CH:8]=[C:7]3[N:26](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:27]=[C:5]1[C:6]=23)([CH3:3])[CH3:2].C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[CH:1]([N:4]1[CH2:13][CH2:12][C:11]2[N:10]=[C:9]([NH:14][C:15]([NH:17][C@@H:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH3:19])=[O:16])[CH:8]=[C:7]3[NH:26][N:27]=[C:5]1[C:6]=23)([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 118271674HCID 118271674, compound

Product 1

HCID 73505440HCID 73505440, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(R)-1-(3-isopropyl-1-trityl-1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridin-7-yl)-3-(1-phenylethyl)urea (75 mg, 0.123 mmol) was taken in TFA (0.5 mL) and stirred at room temperature for 30 minutes before triethylsilane (155 uL, 0.97 mmol) was added. The reaction mixture was stirred for 15 minutes at room temperature then heated at 80° C. for 30 minutes before it 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-isopropyl-1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridin-7-yl)-3-(1-phenylethyl)urea. MS ESI calc'd. for C20H24N6O [M+H]+ 365. found 365. 1H NMR (ppm, 500 MHz, DMSO-d6) δ 7.34-7.23 (m, 4H), 7.18 (m, 1H), 6.40 (s, 1H), 4.90 (m, 1H), 3.40 (m, 2H), 3.22 (m, 2H), 2.90 (m, 1H), 1.38 (d, J=7.0, 3H), 1.07 (d, J=9.4, 6H).

Workup

  1. additionwas added
  2. temperaturethen heated at 80° C. for 30 minutes before it
  3. concentrationwas 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-7952c34faf6d4b0bab1af75a424d1891
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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