Water → HCID 136337180, 화합물

HRID 1428854노트

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HRID 1428854 반응식
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

참가 물질

7

반응물 4

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 136337178HCID 136337178, 화합물HCID 136337179HCID 136337179, 화합물

생성물 2

HCID 136027564HCID 136027564, 화합물HCID 136337180HCID 136337180, 화합물수율 98%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ad298c4d614b4d66bcb02a2183a999f2
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937078B2

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