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 590840ノート

反応式

HRID 590840 の反応式
[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

参加物

4

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

(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).

後処理

  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)

出典と根拠

ORDレコード
ord-627ebd0a9f6e4998ae822930724840fe
出典データセット
uspto-grants-2016_01
特許番号
US09233979B2

反応ノート

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