1,2-Dichloroethane → {(2R)-2-(cyclopentylmethyl)-3-[2-(2,6-dichloro-5-fluoro-4-pyrimidinyl)hydrazino]-3-oxopropyl}[(phenylmethyl)oxy]formamide

HRID 1366713노트

반응식

HRID 1366713 반응식
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([F:9])=[C:4]([NH:10][NH2:11])[N:3]=1.[CH:12]1([CH2:17][C@H:18]([CH2:22][N:23]([CH:32]=[O:33])[O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:19](O)=[O:20])[CH2:16][CH2:15][CH2:14][CH2:13]1.C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1.C(Cl)CCl>CN(C=O)C>[CH:12]1([CH2:17][C@@H:18]([C:19]([NH:11][NH:10][C:4]2[C:5]([F:9])=[C:6]([Cl:8])[N:7]=[C:2]([Cl:1])[N:3]=2)=[O:20])[CH2:22][N:23]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:32]=[O:33])[CH2:16][CH2:15][CH2:14][CH2:13]1

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 21305218(R)-3-(Benzyloxy-formyl-amino)-2-cyclopentylmethyl-propionic acidHCID 866370372,4-Dichloro-5-fluoro-6-hydrazinopyrimidine

생성물 1

HCID 86637038{(2R)-2-(cyclopentylmethyl)-3-[2-(2,6-dichloro-5-fluoro-4-pyrimidinyl)hydrazino]-3-oxopropyl}[(phenylmethyl)oxy]formamide수율 60.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2,4-Dichloro-5-fluoro-6-hydrazinopyrimidine (358 mg 1.817 mmol), (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoic acid (746 mg, 1.508 mmol), and HOAt (247 mg, 1.817 mmol) were dissolved in 15 mL of DMF. NMM (0.798 mL, 7.27 mmol) was added, followed by EDC (348 mg, 1.817 mmol). After stirring overnight at room temperature, the reaction mixture was purified by RP-HPLC to provide {(2R)-2-(cyclopentylmethyl)-3-[2-(2,6-dichloro-5-fluoro-4-pyrimidinyl)hydrazino]-3-oxopropyl}[(phenylmethyl)oxy]formamide (442 mg, 50%). LCMS: (M+H)+: 483.6.

후처리

  1. customthe reaction mixture was purified by RP-HPLC

출처 및 근거

ORD 기록
ord-ff1834e45e994070b0f552c8ab9f6d46
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893056B2

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