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Ammonium formate → (S)-1-[2-(4-hydroxyphenyl)ethyl]-2-methyl-7-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one

HRID 633759
ノート
印刷プレビュー

反応式

HRID 633759 の反応式
C([O-])=O.[NH4+].C([O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][N:21]2[C:25]3=[N:26][C:27]([N:31]4[CH2:37][CH:36]5[O:38][CH:33]([CH2:34][CH2:35]5)[CH2:32]4)=[CH:28][C:29](=[O:30])[N:24]3[CH2:23][C@@:22]2([CH3:43])[C:39]([F:42])([F:41])[F:40])=[CH:15][CH:14]=1)C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-]>[OH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][N:21]2[C:25]3=[N:26][C:27]([N:31]4[CH2:32][CH:33]5[O:38][CH:36]([CH2:35][CH2:34]5)[CH2:37]4)=[CH:28][C:29](=[O:30])[N:24]3[CH2:23][C@@:22]2([CH3:43])[C:39]([F:42])([F:41])[F:40])=[CH:15][CH:14]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 118194495(S)-1-[2-(4-benzyloxyphenyl)ethyl]-2-methyl-7-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one

生成物 1

HCID 72709217(S)-1-[2-(4-hydroxyphenyl)ethyl]-2-methyl-7-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒
HCID 887
Methanol
溶媒

実験手順

700 mg (11.10 mmol) of ammonium formate and 156 mg (0.22 mmol) of 20% palladium hydroxide are added at 0° C. to a solution of 1.20 g (2.22 mmol) of (S)-1-[2-(4-benzyloxyphenyl)ethyl]-2-methyl-7-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one in 15 mL of methanol. The mixture is refluxed for 1 hour and then allowed to cool to room temperature. The reaction medium is filtered through Celite and the filtrate is then evaporated to dryness. After purification by chromatography on silica gel (eluent A/B: DCM/MeOH, gradient A/B: t 0 min 0% B, t 25 min 10% B, t 30 min 10% B), 732 mg of (S)-1-[2-(4-hydroxyphenyl)ethyl]-2-methyl-7-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one were obtained, corresponding to the following characteristics:

後処理

  1. temperatureThe mixture is refluxed for 1 hour
  2. filtrationThe reaction medium is filtered through Celite
  3. customthe filtrate is then evaporated to dryness
  4. customAfter purification by chromatography on silica gel (eluent A/B: DCM/MeOH, gradient A/B: t 0 min 0% B, t 25 min 10% B, t 30 min 10% B), 732 mg of (S)-1-[2-(4-hydroxyphenyl)ethyl]-2-methyl-7-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one
  5. customwere obtained, corresponding to the following characteristics

出典と根拠

ORDレコード
ord-c245a8dcb4434ed4967f845a31b1c463
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09321790B2

反応ノート

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