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Triethylamine → N-[4-chloro-2-[(E)-hydroxyiminomethyl]-5-[4-[3-(2-methoxyphenyl)-5-methyl-1,2-oxazole-4-carbonyl]piperazin-1-yl]phenyl]-4-(dimethylamino)benzamide

HRID 1808900
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HRID 1808900 반응식
[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[C:17]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][CH3:29])=[N:18][O:19][C:20]=3[CH3:21])=[O:15])[CH2:10][CH2:9]2)=[CH:6][C:5]([NH:30][C:31](=[O:41])[C:32]2[CH:37]=[CH:36][C:35]([N:38]([CH3:40])[CH3:39])=[CH:34][CH:33]=2)=[C:4]([CH:42]=O)[CH:3]=1.Cl.[NH2:45][OH:46].C(N(CC)CC)C>CN(C=O)C.CO.C(Cl)Cl>[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[C:17]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][CH3:29])=[N:18][O:19][C:20]=3[CH3:21])=[O:15])[CH2:10][CH2:9]2)=[CH:6][C:5]([NH:30][C:31](=[O:41])[C:32]2[CH:33]=[CH:34][C:35]([N:38]([CH3:40])[CH3:39])=[CH:36][CH:37]=2)=[C:4](/[CH:42]=[N:45]/[OH:46])[CH:3]=1
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참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 86670897N-(4-chloro-2-formyl-5-(4-(3-(2-methoxyphenyl)-5-methylisoxazole-4-carbonyl)piperazin-1-yl)phenyl)-4-(dimethylamino)benzamide

생성물 1

HCID 87113030N-[4-chloro-2-[(E)-hydroxyiminomethyl]-5-[4-[3-(2-methoxyphenyl)-5-methyl-1,2-oxazole-4-carbonyl]piperazin-1-yl]phenyl]-4-(dimethylamino)benzamide수율 33.7%

시약·촉매·용매 3

HCID 887Methanol용매
HCID 6228Dimethylformamide용매
HCID 6344Dichloromethane용매

실험 절차

The reaction mixture of N-(4-chloro-2-formyl-5-(4-(3-(2-methoxyphenyl)-5-methylisoxazole-4-carbonyl)piperazin-1-yl)phenyl)-4-(dimethylamino)benzamide (Example 115, 7.7 mg, 0.013 mmol), hydroxylamine hydrochloride (1.8 mg, 0.026 mmol) and triethylamine (3.6 μL, 0.026 mmol) in DMF (1.2 mL), MeOH (0.240 mL) and DCM (0.240 mL) was stirred at RT overnight. The product was purified by preparative HPLC (10 mM NH4OAc AcCN/H2O) to give 2.7 mg of the title compound. 1H-NMR (DMSO-d6, 400 MHz) δ 11.46 (1H, br. s.), 8.48 (1H, s), 8.31 (1H, s), 7.87 (2H, d, J=9.0 Hz), 7.58 (1H, s), 7.55-7.44 (2H, m), 7.18 (1H, d, J=8.3 Hz), 7.10 (1H, t, J=7.5 Hz), 6.81 (2H, d, J=9.0 Hz), 3.75 (3H, s), 3.03 (6H, s). HPLC/MS (Method H): (ES+) m/z (M+H)+=617; Rt=1.98 min.

후처리

  1. customThe product was purified by preparative HPLC (10 mM NH4OAc AcCN/H2O)

출처 및 근거

ORD 기록
ord-a7922dd441924a58b67f13a5ca183c06
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08362004B2

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