Sodium Hydroxide → 5-(4-{5-[(4-Fluorophenyl)methyl]-6-methylpyrimidin-4-yl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1,3-thiazol-2-amine

HRID 241095ノート

反応式

HRID 241095 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[C:10]([N:16]3[CH2:22][C:21]4[CH:23]=[C:24]([C:27]5[S:31][C:30]([NH:32]C(=O)C)=[N:29][CH:28]=5)[CH:25]=[CH:26][C:20]=4[O:19][CH2:18][CH2:17]3)=[N:11][CH:12]=[N:13][C:14]=2[CH3:15])=[CH:4][CH:3]=1.[OH-].[Na+]>Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[C:10]([N:16]3[CH2:22][C:21]4[CH:23]=[C:24]([C:27]5[S:31][C:30]([NH2:32])=[N:29][CH:28]=5)[CH:25]=[CH:26][C:20]=4[O:19][CH2:18][CH2:17]3)=[N:11][CH:12]=[N:13][C:14]=2[CH3:15])=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 86647839N-[5-(4-{5-[(4-fluorophenyl)methyl]-6-methylpyrimidine-4-yl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1,3-thiazol-2-yl]acetamide

生成物 1

HCID 595866555-(4-{5-[(4-Fluorophenyl)methyl]-6-methylpyrimidin-4-yl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1,3-thiazol-2-amine収率 64.1%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

A solution of N-[5-(4-{5-[(4-fluorophenyl)methyl]-6-methylpyrimidine-4-yl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1,3-thiazol-2-yl]acetamide (75 mg, 0.15 mmol) in 6 N hydrochloric acid (4 mL) was stirred at 95° C. for 15 h. After cooling to room temperature the mixture was neutralized with 50% aqueous sodium hydroxide, concentrated to dryness, and the solid residue extracted with ethanol (3×10 mL). Evaporation of the solvent and purification of the residue by preparative HPLC afforded 5-(4-{5-[(4-fluorophenyl)methyl]-6-methylpyrimidin-4-yl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1,3-thiazol-2-amine (43 mg, 62% yield) as a colorless solid. 1H NMR (400 MHz, CD3OD): 8.46 (s, 1H), 7.21 (m, 1H), 7.11 (m, 4H), 6.98 (s, 1H), 6.90 (d, 1H), 6.61 (m, 1H), 4.46 (s, 2H), 4.26 (ms, 2H), 3.97 (s, 2H), 3.87 (m, 2H), 2.21 (s, 3H); MS (EI) C24H22FN5OS: 448 (MH+).

後処理

  1. concentrationconcentrated to dryness
  2. extractionthe solid residue extracted with ethanol (3×10 mL)
  3. customEvaporation of the solvent and purification of the residue by preparative HPLC

出典と根拠

ORDレコード
ord-5c834141dc894ee997f56c7a25529e71
出典データセット
uspto-grants-2014_02
特許番号
US08648066B2

反応ノート

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