Water → HCID 136337180、化合物

HRID 1428854ノート

反応式

HRID 1428854 の反応式
O.[OH-].[Li+].O.C([O:7][C:8]([C:10]1[CH:11]=[N:12][N:13]([C:15]2[NH:24][C:23](=[O:25])[C:22]3[C:17](=[CH:18][C:19]4[CH2:28][CH2:27][CH2:26][C:20]=4[CH:21]=3)[N:16]=2)[CH:14]=1)=[O:9])C.C([O:31][C:32]([C:34]1[CH:35]=[N:36][N:37]([C:39]2[NH:48][C:47](=[O:49])[C:46]3[C:45]4[CH2:50][CH2:51][CH2:52][C:44]=4[CH:43]=[CH:42][C:41]=3[N:40]=2)[CH:38]=1)=[O:33])C>C1COCC1>[O:25]=[C:23]1[C:22]2[C:21]3[CH2:20][CH2:26][CH2:27][C:28]=3[CH:19]=[CH:18][C:17]=2[N:16]=[C:15]([N:13]2[CH:14]=[C:10]([C:8]([OH:7])=[O:9])[CH:11]=[N:12]2)[NH:24]1.[O:49]=[C:47]1[C:46]2[C:41](=[CH:42][C:43]3[CH2:44][CH2:52][CH2:51][C:50]=3[CH:45]=2)[N:40]=[C:39]([N:37]2[CH:38]=[C:34]([C:32]([OH:31])=[O:33])[CH:35]=[N:36]2)[NH:48]1

参加物

7

反応物 4

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 136337178HCID 136337178、化合物HCID 136337179HCID 136337179、化合物

生成物 2

HCID 136027564HCID 136027564、化合物HCID 136337180HCID 136337180、化合物収率 98%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Lithium hydroxide monohydrate (0.611 g, 14.6 mmol) and water (9.1 mL) were added to a 10:1 mixture of 1-(4-oxo-4,6,7,8-tetrahydro-3H-cyclopenta[g]quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester and 1-(1-oxo-2,7,8,9-tetrahydro-1H-cyclopenta[f]quinazolin-3-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (1.18 g, 0.228 mmol) in THF (13.6 mL) and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated and the residue was redissolved in water (20 mL). This solution was brought to pH 1 with 1M aqueous HCl. The resulting precipitate was collected and dried to yield a 10:1 mixture of the titled compound and 1-(1-oxo-2,7,8,9-tetrahydro-1H-cyclopenta[f]quinazolin-3-yl)-1H-pyrazole-4-carboxylic acid (1.05 g, 98% yield). A portion of the precipitate (0.511 g) was triturated twice from 10 mL DMSO to yield a pure sample of the titled compound (0.310 g, 61% recovery). MS (ESI/Cl): mass calcd. for C15H12N4O3, 296.1; m/z found, 297.1 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 13.00 (s, 1H), 12.68 (s, 1H), 8.93 (s, 1H), 8.24 (s, 1H), 7.96 (s, 1H), 7.52 (s, 1H), 3.05-2.93 (m, 4H), 2.09 (p, J=7.4 Hz, 2H).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was redissolved in water (20 mL)
  3. customThe resulting precipitate was collected
  4. customdried
  5. customto yield

出典と根拠

ORDレコード
ord-ad298c4d614b4d66bcb02a2183a999f2
出典データセット
uspto-grants-2015_01
特許番号
US08937078B2

反応ノート

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