HRID2069857

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6344

Dichloromethane

CH2Cl2

HCID4311764

Sodium borohydride (Na(BH4))

H4BNa

结构：Cn1cc(-c2cccc(-n3ncc4cc(C(C)(C)C)cc(F)c4c3=O)c2C=O)cc(Nc2ccc(C(=O)N3CCOCC3)cn2)c1=O

HCID59473809

未命名化合物

PRODUCTS

生成物

HCID46866598

未命名化合物

收率 75.1%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID887

Methanol

CH4O

PROCEDURE

实验过程

69 mg of 2-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-6-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-benzaldehyde was weighed into a 20 mL reaction vial fitted with a stir bar and cap. Added 2 mL of CH2Cl2 and 2 mL MeOH and stirred to obtain a clear amber solution. Added 14 mg of sodium borohydride. Stirred at room temperature for 3 hr. Quenched with 5 mL of saturated aqueous NH4Cl. Separated phases and extracted the aqueous phase with 2×2 mL CH2Cl2. Washed the combined organic phases with 5 mL of saturated aqueous NaHCO3. Dried over Na2SO4 and removed the solvent on rotavap. Crystallized the residue from isopropyl acetate to obtain 52 mg of the title compound as a white solid. MS (ESI) 639 (M+H)+.

WORKUP

后处理

customvial fitted with a stir bar
customcap
customto obtain a clear amber solution
stirringStirred at room temperature for 3 hr
customQuenched with 5 mL of saturated aqueous NH4Cl
extractionSeparated phases and extracted the aqueous phase with 2×2 mL CH2Cl2
washWashed the combined organic phases with 5 mL of saturated aqueous NaHCO3
dry with materialDried over Na2SO4
customremoved the solvent on rotavap
customCrystallized the residue from isopropyl acetate

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-f8c9c03373094c8a82041b0afad19266
来源数据集: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08299077B2
来源说明: uspto-grants-2012_10

反应 SMILES

[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]3[CH:30]=[C:29]([NH:31][C:32]4[CH:37]=[CH:36][C:35]([C:38]([N:40]5[CH2:45][CH2:44][O:43][CH2:42][CH2:41]5)=[O:39])=[CH:34][N:33]=4)[C:28](=[O:46])[N:27]([CH3:47])[CH:26]=3)[C:18]=1[CH:19]=[O:20])[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.[BH4-].[Na+]>CO>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]3[CH:30]=[C:29]([NH:31][C:32]4[CH:37]=[CH:36][C:35]([C:38]([N:40]5[CH2:45][CH2:44][O:43][CH2:42][CH2:41]5)=[O:39])=[CH:34][N:33]=4)[C:28](=[O:46])[N:27]([CH3:47])[CH:26]=3)[C:18]=1[CH2:19][OH:20])[N:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]