Hydrochloric Acid → HCID 86667427、化合物

HRID 526997ノート

反応式

HRID 526997 の反応式
[NH2:1][CH2:2][C@:3]1([OH:18])[CH2:8][CH2:7][CH2:6][C@H:5]([NH:9][C:10]2[C:15]([F:16])=[CH:14][N:13]=[C:12]([Cl:17])[N:11]=2)[CH2:4]1.CCN(C(C)C)C(C)C.[C:28](Cl)(=[O:30])[CH3:29].Cl.[OH-].[Na+]>ClCCl>[Cl:17][C:12]1[N:11]=[C:10]([NH:9][C@H:5]2[CH2:6][CH2:7][CH2:8][C@:3]([CH2:2][NH:1][C:28](=[O:30])[CH3:29])([OH:18])[CH2:4]2)[C:15]([F:16])=[CH:14][N:13]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 86667425(1S,3S)-1-(aminomethyl)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)cyclohexanol2 回

生成物 1

HCID 86667427HCID 86667427、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(1S,3S)-1-(aminomethyl)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)cyclohexanol, 46b, (0.19 g, 0.69 mmol) was dissolved in dichloromethane (15 mL) and treated with DIPEA (1.20 mL, 6.91 mmol) and acetyl chloride (0.10 mL, 1.38 mmol). After 5 minutes, the reaction mixture was diluted into 1N HCl (30 mL), and the aqueous layer was brought to a basic pH by addition of 1N NaOH. The resulting suspension was extracted with dichloromethane (50 mL). The organic layer was dried on Na2SO4 and concentrated in vacuo to provide the crude product, which was purified by silica gel chromatography (20-100% EtOAc/hexanes gradient) to afford 195 mg of N-{[(1S,3S)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)-1-hydroxycyclo-hexyl]methyl}acetamide as a white foamy solid. LCMS RT=2.82 (M+1) 317.33.

後処理

  1. extractionThe resulting suspension was extracted with dichloromethane (50 mL)
  2. customThe organic layer was dried on Na2SO4
  3. concentrationconcentrated in vacuo
  4. customto provide the crude product, which
  5. customwas purified by silica gel chromatography (20-100% EtOAc/hexanes gradient)

出典と根拠

ORDレコード
ord-f6c064fb3d2140638abe22d38d6426fe
出典データセット
uspto-grants-2016_05
特許番号
US09345708B2

反応ノート

読み込み中…