2-[(1R)-1-Chloroethyl]-3-fluoropyridine → HCID 25064543、化合物

HRID 1694547ノート

反応式

HRID 1694547 の反応式
[NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:12][OH:13])=[N:8][C:7]([SH:18])=[N:6][C:5]=2[N:19]=1.Cl[C@@H:21]([C:23]1[C:28]([F:29])=[CH:27][CH:26]=[CH:25][N:24]=1)[CH3:22]>>[NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH2:14][CH:15]([CH3:16])[CH3:17])[CH2:12][OH:13])=[N:8][C:7]([S:18][C@H:21]([C:23]3[C:28]([F:29])=[CH:27][CH:26]=[CH:25][N:24]=3)[CH3:22])=[N:6][C:5]=2[N:19]=1

参加物

3

反応物 2

HCID 598688232-[(1R)-1-Chloroethyl]-3-fluoropyridineHCID 178445911HCID 178445911、化合物

生成物 1

HCID 25064543HCID 25064543、化合物収率 47%

実験手順

The title compound was prepared using General method A starting from (2R)-2-[(2-amino-5-mercapto[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol (348 mg, 1.16 mmol) and 2-((R)-1-chloroethyl)-3-fluoro-pyridine (240 mg, 1.5 mmol). Purification by flash column chromatography (eluent DCM:methanol gradient) resulted in 190 mg (47% yield) of the title compound with a diastereomeric excess of 60%. Of this material 55 mg was further purified by preparative HPLC. The last eluting isomer was collected to yield 21 mg of the title compound.

後処理

  1. customThe title compound was prepared
  2. customPurification by flash column chromatography (eluent DCM:methanol gradient)

出典と根拠

ORDレコード
ord-dd564f6d6bd24c8692feb446c2775d99
出典データセット
uspto-grants-2012_04
特許番号
US08158785B2

反応ノート

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