Lithium hydroxide, monohydrate → HCID 10434480、化合物

HRID 1353513ノート

反応式

HRID 1353513 の反応式
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][CH:18]([C:39]([O:41]C)=[O:40])[NH:19][C:20]([N:22]3[CH2:27][CH2:26][CH:25]([N:28]4[CH2:37][C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[NH:30][C:29]4=[O:38])[CH2:24][CH2:23]3)=[O:21])=[CH:14][CH:15]=2)[CH:10]=[N:9]1)=O)(C)(C)C.O.[OH-].[Li+]>O1CCCC1.CO.O>[NH:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][CH:18]([NH:19][C:20]([N:22]3[CH2:27][CH2:26][CH:25]([N:28]4[CH2:37][C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[NH:30][C:29]4=[O:38])[CH2:24][CH2:23]3)=[O:21])[C:39]([OH:41])=[O:40])=[CH:14][CH:15]=2)[CH:10]=[N:9]1

参加物

6

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 58864391HCID 58864391、化合物

生成物 1

HCID 10434480HCID 10434480、化合物収率 80.5%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of 5-(2-methoxycarbonyl-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-ethyl)-indazole-1-carboxylic acid tert-butyl ester (168 mg, 0.29 mmol) was dissolved in tetrahydrofuran (5 mL) in methanol (5 mL) was cooled to 0° C. A solution of lithium hydroxide monohydrate (49 mg, 2.04 mmol) in water (5 mL) was added. The reaction mixture was stirred at 0° C. for 6 h and then placed in the freezer for a further 16 h. The solvents were removed in vacuo and the residue dissolved in water (15 mL). The pH of the aqueous solution was adjusted to ca. 1 with 1N hydrochloric acid. The resulting white solid precipitated was collected by filtration. The solid was dried under vacuum to give the title compound (108 mg, 80%). 1H-NMR (DMSO-d6, 300 MHz) δ 12.94 (bs, 1H), 9.19 (s, 1H), 8.01 (s, 1H), 7.61 (s, 1H), 7.46 (d, J=8.4 Hz, 1H), 7.28 (dd, J=8.5, 1.5 Hz, 1H), 7.13–7.06 (m, 2H), 6.86 (t, J=7.0 Hz, 1H), 6.76–6.72 (m, 2H), 4.32–4.24 (m, 2H), 4.09–4.02 (m, 4H), 3.17–2.97 (m, 2H), 2.72–2.59 (m, 2H), 1.57–1.35 (m, 4H). IR (KBr, cm−1) 3424, 2963, 2930, 1660, 1628, 1505, 1474, 1446, 753. Mass spec.: 463 (MH)+.

後処理

  1. waitplaced in the freezer for a further 16 h
  2. customThe solvents were removed in vacuo
  3. dissolutionthe residue dissolved in water (15 mL)
  4. customThe resulting white solid precipitated
  5. filtrationwas collected by filtration
  6. customThe solid was dried under vacuum

出典と根拠

ORDレコード
ord-0edf3aa6fcc0433cac4aaa8c139375d2
出典データセット
uspto-grants-2007_05
特許番号
US07220862B2

反応ノート

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