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

HRID 1366713ノート

反応式

HRID 1366713 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  1. customthe reaction mixture was purified by RP-HPLC

出典と根拠

ORDレコード
ord-ff1834e45e994070b0f552c8ab9f6d46
出典データセット
uspto-grants-2011_02
特許番号
US07893056B2

反応ノート

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