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

HRID 590838Notes

Reaction equation

HRID 590838 reaction equation
COC1C=CC(C[N:8]2[CH2:17][CH2:16][C:15]3[N:14]=[C:13]([NH:18][C:19]([NH:21][C@@H:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH3:23])=[O:20])[CH:12]=[C:11]4[N:30](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[N:31]=[C:9]2[C:10]=34)=CC=1.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[C:24]1([C@H:22]([NH:21][C:19]([NH:18][C:13]2[CH:12]=[C:11]3[NH:30][N:31]=[C:9]4[C:10]3=[C:15]([CH2:16][CH2:17][NH:8]4)[N:14]=2)=[O:20])[CH3:23])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 118271755(R)-1-(3-(4-methoxybenzyl)-1-trityl-1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridin-7-yl)-3-(1-phenylethyl)urea

Product 1

HCID 136236929(R)-1-(1-phenylethyl)-3-(1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridin-7-yl)urea

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(R)-1-(3-(4-methoxybenzyl)-1-trityl-1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridin-7-yl)-3-(1-phenylethyl)urea (22 mg, 0.032 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) stirred for 15 minutes at room temperature then heated to 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-(1-phenylethyl)-3-(1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridin-7-yl)urea. MS ESI calc'd. for C17H18N6O [M+H]+ 323. found 323. 1H NMR (ppm, 500 MHz, DMSO-d6) δ 8.98 (s, 1H), 8.45 (br, s, 1H), 7.38 (m, 4H), 7.20 (m, 1H), 7.00 (s, 1H), 6.23 (s, 1H), 4.83 (m, 1H), 3.42 (dd, J=8.0, 5.0 Hz, 2H), 2.80 (dd, J=8.0, 5.0 Hz, 2H), 1.40 (d, J=11 Hz, 3H).

Workup

  1. stirringstirred for 15 minutes at room temperature
  2. temperaturethen heated to 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-9065dd7cb19f4ca9bac96d0902c63120
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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