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Potassium Carbonate → (S)-4-(2-(4-fluorobenzylamino)-4-(tetrahydrofuran-3-yloxy)quinazolin-6-yl)-N-(2-(dimethylamino)ethyl)benzamide

HRID 1187276
ノート
印刷プレビュー

反応式

HRID 1187276 の反応式
[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8]2[N:17]=[C:16]([O:18][C@H:19]3[CH2:23][CH2:22][O:21][CH2:20]3)[C:15]3[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:33][N:34]([CH3:49])[CH2:35][CH2:36][NH:37][C:38]([C:40]1[CH:45]=[CH:44][C:43](B(O)O)=[CH:42][CH:41]=1)=[O:39]>CN(C=O)C.O>[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8]2[N:17]=[C:16]([O:18][C@H:19]3[CH2:23][CH2:22][O:21][CH2:20]3)[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:43]4[CH:44]=[CH:45][C:40]([C:38]([NH:37][CH2:36][CH2:35][N:34]([CH3:33])[CH3:49])=[O:39])=[CH:41][CH:42]=4)[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 44118750(4-((2-(Dimethylamino)ethyl)carbamoyl)phenyl)boronic acidHCID 59359761(S)-N-(4-fluorobenzyl)-6-bromo-4-(tetrahydrofuran-3-yloxy)quinazolin-2-amine

生成物 1

HCID 59359767(S)-4-(2-(4-fluorobenzylamino)-4-(tetrahydrofuran-3-yloxy)quinazolin-6-yl)-N-(2-(dimethylamino)ethyl)benzamide収率 64.5%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 6228Dimethylformamide溶媒

実験手順

(S)—N-(4-fluorobenzyl)-6-bromo-4-(tetrahydrofuran-3-yloxy)quinazolin-2-amine (50 mg, 0.12 mmol), potassium carbonate (33 mg, 0.24 mmol), tetrakis(triphenyl-phosphine)palladium (8 mg, 0.007 mmol) and 4-((2-(dimethylamino)ethyl)-carbamoyl)phenylboronic acid (36 mg, 0.132 mmol) in DMF (1.0 mL) and water (0.3 mL) was heated to 150° C. for 10 minutes under microwave irradiation. Solvents were concentrated in vacuo and the residue was purified by RP HPLC, using a C18 column with a gradient of 0.1% H2O, 0.1% TFA-acetonitrile, to provide the desired product (41 mg) which was characterized by its mass spectrum as follows: MS (m/z): 530 ([M+H]+, 100); HPLC Rt=1.26 minutes (Method B).

後処理

  1. concentrationSolvents were concentrated in vacuo
  2. customthe residue was purified by RP HPLC

出典と根拠

ORDレコード
ord-6db9abb1b12c460b9fcf8f0c522ae975
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08673929B2

反応ノート

読み込み中…

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