Potassium Phosphate, Tribasic → 3-{[(Benzyloxy)carbonyl]amino}-7-(3-oxopiperazin-1-yl)quinoline-2-carboxylic acid

HRID 924488노트

반응식

HRID 924488 반응식
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([C:23]([O:25]CC)=[O:24])=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17](Br)[CH:16]=2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:28]1[CH2:33][CH2:32][NH:31][CH2:30][C:29]1=[O:34].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC(C)C)=CC=CC=2OC(C)C)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(O)(C)(C)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([C:23]([OH:25])=[O:24])=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17]([N:31]1[CH2:32][CH2:33][NH:28][C:29](=[O:34])[CH2:30]1)[CH:16]=2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 231360Piperazin-2-oneHCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenylHCID 86726857Ethyl 3-(((benzyloxy)carbonyl)amino)-7-bromoquinoline-2-carboxylate

생성물 1

HCID 867269333-{[(Benzyloxy)carbonyl]amino}-7-(3-oxopiperazin-1-yl)quinoline-2-carboxylic acid수율 7%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6386tert-Butanol용매

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온도
100 °C

실험 절차

A mixture of ethyl 3-{[(benzyloxy)carbonyl]amino}-7-bromoquinoline-2-carboxylate (250 mg, 0.58 mmol), piperazin-2-one (120 mg, 1.2 mmol), Pd(OAc)2 (20 mg), dicyclohexyl(2′,6′-diisopropoxybiphenyl-2-yl)phosphine (41 mg, 0.087 mmol), and K3PO4 (490 mg, 2.3 mmol) in tert-butyl alcohol (8 mL) was deoxygenated and purged with nitrogen then heated at 100° C. in a sealed vial for 3 h. To the mixture resulting mixture, 20 mL of EtOAc and 20 mL of water were added. The precipitates collected by filtration and purified by preparative HPLC (XBridge™ C18 column, eluting with a gradient of MeCN/water containing 0.1% NH4OH, at a flow rate of 60 mL/min.) to afford the sub-title compound (0.017 g, 6.9%). LCMS calc. for C22H21N4O5 [M+H]+: m/z=421.1. found: 421.2.

후처리

  1. customwas deoxygenated
  2. custompurged with nitrogen
  3. customTo the mixture resulting mixture, 20 mL of EtOAc and 20 mL of water
  4. additionwere added
  5. filtrationThe precipitates collected by filtration
  6. custompurified by preparative HPLC (XBridge™ C18 column
  7. washeluting with a gradient of MeCN/water containing 0.1% NH4OH, at a flow rate of 60 mL/min.)

출처 및 근거

ORD 기록
ord-6224b23484c44d41bfe765af2228da91
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278950B2

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