Triethylamine → 4-(2-Fluoro-4-(2-fluoro-5-methylbenzamido)phenoxy)-5-methyl-N-(2-morpholinoethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide, hydrochloride salt

HRID 2117111ノート

反応式

HRID 2117111 の反応式
[NH2:1][C:2]1[CH:29]=[CH:28][C:5]([O:6][C:7]2[C:12]3=[C:13]([CH3:27])[C:14]([C:16]([NH:18][CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[O:17])=[CH:15][N:11]3[N:10]=[CH:9][N:8]=2)=[C:4]([F:30])[CH:3]=1.CCN(CC)CC.[F:38][C:39]1[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][C:40]=1[C:41]([Cl:43])=[O:42]>C1COCC1>[ClH:43].[F:30][C:4]1[CH:3]=[C:2]([NH:1][C:41](=[O:42])[C:40]2[CH:44]=[C:45]([CH3:48])[CH:46]=[CH:47][C:39]=2[F:38])[CH:29]=[CH:28][C:5]=1[O:6][C:7]1[C:12]2=[C:13]([CH3:27])[C:14]([C:16]([NH:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[O:17])=[CH:15][N:11]2[N:10]=[CH:9][N:8]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 70180482-Fluoro-5-methylbenzoyl chlorideHCID 210816664-(4-Amino-2-fluorophenoxy)-5-methyl-N-(2-morpholinoethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide

生成物 1

HCID 1317262434-(2-Fluoro-4-(2-fluoro-5-methylbenzamido)phenoxy)-5-methyl-N-(2-morpholinoethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide, hydrochloride salt収率 23%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 4-(4-amino-2-fluorophenoxy)-5-methyl-N-(2-morpholinoethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide (25 mg, 0.06 mmol) in 1 mL of THF were added Et3N (0.2 mL) and a solution of 2-fluoro-5-methylbenzoyl chloride (20 mg, 0.11 mmol) in 1 mL of THF at room temperature. The mixture was allowed to stir for 1 h and HPLC analysis indicated the consumption of the starting material. The reaction was quenched with MeOH. The solution was then concentrated in vacuo and the residue was purified by preparative HPLC to give the title compound (8.0 mg, 23%) as a HCl salt. 1H NMR (CD3OD) δ 8.48 (d, 1H), 7.83 (m, 3H), 7.28 (m, 3H), 7.00 (m, 1H), 2.90-4.00 (m, 12H), 2.76 (s, 3H), 2.33 (s, 3H); MS(ESI+) m/z 551.2 (M+H)+.

後処理

  1. customat room temperature
  2. customthe consumption of the starting material
  3. customThe reaction was quenched with MeOH
  4. concentrationThe solution was then concentrated in vacuo
  5. customthe residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-cbdc2f66d7c9406ab9e89d896adf355b
出典データセット
uspto-grants-2008_10
特許番号
US07439246B2

反応ノート

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