Triethylsilane → (S)-1-(2-hydroxy-2-methyl-1-phenylpropyl)-3-(1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridin-7-yl)urea

HRID 590840노트

반응식

HRID 590840 반응식
[OH:1][C:2]([CH3:55])([CH3:54])[C@@H:3]([NH:10][C:11]([NH:13][C:14]1[CH:23]=[C:22]2[N:24](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:25]=[C:20]3[C:21]2=[C:16]([CH2:17][CH2:18][N:19]3CC2C=CC(OC)=CC=2)[N:15]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[OH:1][C:2]([CH3:55])([CH3:54])[C@@H:3]([NH:10][C:11]([NH:13][C:14]1[CH:23]=[C:22]2[NH:24][N:25]=[C:20]3[C:21]2=[C:16]([CH2:17][CH2:18][NH:19]3)[N:15]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

4

반응물 2

HCID 12052TriethylsilaneHCID 118381006(S)-1-(2-hydroxy-2-methyl-1-phenylpropyl)-3-(3-(4-methoxybenzyl)-1-trityl-1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridin-7-yl)urea

생성물 1

HCID 136236930(S)-1-(2-hydroxy-2-methyl-1-phenylpropyl)-3-(1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridin-7-yl)urea

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

(S)-1-(2-hydroxy-2-methyl-1-phenylpropyl)-3-(3-(4-methoxybenzyl)-1-trityl-1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridin-7-yl)urea (38 mg, 0.052 mmol) was taken in TFA (0.17 mL) and stirred at room temperature for 30 minutes. To the reaction was added triethylsilane (34 uL, 0.209 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 (S)-1-(2-hydroxy-2-methyl-1-phenylpropyl)-3-(1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridin-7-yl)urea. MS ESI calc'd. for C19H22N6O2 [M+H]+ 367. found 367. 1H NMR (ppm, 500 MHz, DMSO-d6) δ 9.25 (br, 2H), 7.28 (m, 4H), 7.20 (m, 1H), 6.90 (s, 1H), 4.59 (d, J=14 Hz, 1H), 3.42 (dd, J=8.0, 5.0 Hz, 2H), 2.92 (dd, J=8.0, 5.0 Hz, 2H), 1.95 (s, 3H), 1.0 (s, 3H).

후처리

  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)

출처 및 근거

ORD 기록
ord-627ebd0a9f6e4998ae822930724840fe
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233979B2

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