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Hydrochloric Acid → (R)-tetrahydrofuran-3-yl ((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate hydrochloride

HRID 2079356
ノート
印刷プレビュー

反応式

HRID 2079356 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:17]=[C:16]([N:18]2[CH2:23][CH2:22][CH2:21][C@@H:20]([CH2:24][NH:25][C:26](=[O:33])[O:27][C@@H:28]3[CH2:32][CH2:31][O:30][CH2:29]3)[CH2:19]2)[C:15]2[C:10](=[CH:11][C:12]([CH3:34])=[CH:13][CH:14]=2)[N:9]=1.[ClH:35]>C(Cl)Cl.CCOCC>[ClH:35].[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:17]=[C:16]([N:18]2[CH2:23][CH2:22][CH2:21][C@@H:20]([CH2:24][NH:25][C:26](=[O:33])[O:27][C@@H:28]3[CH2:32][CH2:31][O:30][CH2:29]3)[CH2:19]2)[C:15]2[C:10](=[CH:11][C:12]([CH3:34])=[CH:13][CH:14]=2)[N:9]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 136121430(R)-Tetrahydrofuran-3-yl((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate

生成物 1

HCID 136330115(R)-tetrahydrofuran-3-yl ((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate hydrochloride収率 70%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回
HCID 6344
Dichloromethane
溶媒

実験手順

(R)-Tetrahydrofuran-3-yl ((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate (116 mg, 0.251 mmol) was suspended in 8 mL anhydrous CH2Cl2 and gently heated until an homogenous solution was formed. After the reaction was cooled to room temperature, a 2.0 M solution of HCl in Et2O (0.126 mL, 0.251 mmol) was added in one portion. The reaction mixture was diluted with 25 mL Et2O, and the product precipitated from solution. The reaction was stirred for an additional 30 minutes before the solid was filtered and dried to obtain (R)-tetrahydrofuran-3-yl ((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate hydrochloride as a light yellow solid (99 mg, 70%). LC/MS: m/z 463.5 (M+H)+ at 2.37 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)). 1H NMR (400 MHz, DMSO-d6) δ 8.22 (d, J=7.7 Hz, 1H), 7.95 (d, J=8.5 Hz, 1H), 7.75 (s, 1H), 7.42-7.49 (m, 3H), 6.97-7.08 (m, 2H), 5.08 (dd, J=6.1, 4.6 Hz, 1H), 4.52-4.54 (m, 2H), 3.66-3.78 (m, 3H), 3.58-3.60 (m, 1H), 3.48 (t, J=10.7 Hz, 1H), 3.23 (t, J=11.5 Hz, 1H), 3.00 (t, J=6.3 Hz, 2H), 2.53 (s, 3H), 2.05-2.14 (m, 1H), 1.80-1.91 (m, 4H), 1.72 (d, J=9.0 Hz, 1H), 1.34-1.43 (m, 1H) ppm.

後処理

  1. temperaturegently heated until an homogenous solution
  2. customwas formed
  3. customthe product precipitated from solution
  4. filtrationwas filtered
  5. customdried

出典と根拠

ORDレコード
ord-c95fbeedf7d140a59114420509023492
出典データセット
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07928107B2

反応ノート

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