Water → (1R,2R)-N1-[3,6-dicyclopropyl-5-(2,4-dichlorophenyl)pyrazin-2-yl]-2,3-dihydro-1H-indene-1,2-diamine

HRID 1612354

反応式

HRID 1612354 の反応式
[N:1]([C@@H:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C@H:5]1[NH:13][C:14]1[C:19]([CH:20]2[CH2:22][CH2:21]2)=[N:18][C:17]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[Cl:30])=[C:16]([CH:31]2[CH2:33][CH2:32]2)[N:15]=1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>C1COCC1>[CH:20]1([C:19]2[C:14]([NH:13][C@@H:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH2:12][C@H:4]3[NH2:1])=[N:15][C:16]([CH:31]3[CH2:32][CH2:33]3)=[C:17]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=3[Cl:30])[N:18]=2)[CH2:21][CH2:22]1

参加物

5

反応物 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 58583346N-[(1R,2R)-2-azido-2,3-dihydro-1H-inden-1-yl]-3,6-dicyclopropyl-5-(2,4-dichlorophenyl)pyrazin-2-amine

生成物 1

HCID 58583281(1R,2R)-N1-[3,6-dicyclopropyl-5-(2,4-dichlorophenyl)pyrazin-2-yl]-2,3-dihydro-1H-indene-1,2-diamine収率 100.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of N-[(1R,2R)-2-azido-2,3-dihydro-1H-inden-1-yl]-3,6-dicyclopropyl-5-(2,4-dichlorophenyl)pyrazin-2-amine (0.55 g, 1.15 mmol) in anhydrous THF (30 mL) was added PPh3 (0.396 g, 1.51 mmol). The resulting mixture was stirred at rt for 3 hr. To the solution was added water (0.25 mL, 13.9 mmol). The reaction is then allowed to stir overnight at rt. The mixture is concentrated, and the resulting solid is dissolved in MeOH. Purify by passage over Biorad acidic resin by applying the MeOH solution onto the resin and rinsing the resin with MeOH. The resin was then rinsed with 5% triethylamine/MeOH solution to afford 0.52 g (75%) of (1R,2R)-N1-[3,6-dicyclopropyl-5-(2,4-dichlorophenyl)pyrazin-2-yl]-2,3-dihydro-1H-indene-1,2-diamine as a solid: 1H NMR (CDCl3) δ 0.85-1.12, 1.64-1.76, 1.89, 2.68-2.82, 3.31-3.39, 3.66-3.72, 5.16, 5.33, 7.28-7.53; MS (ESI+) for C25H24Cl2N4 m/z 451 (M+H)+.

後処理

  1. stirringto stir overnight at rt
  2. concentrationThe mixture is concentrated
  3. dissolutionthe resulting solid is dissolved in MeOH
  4. customPurify by passage over Biorad acidic resin
  5. washrinsing the resin with MeOH
  6. washThe resin was then rinsed with 5% triethylamine/MeOH solution

出典と根拠

ORDレコード
ord-f23a97bae0e24791abe92ce475928c21
出典データセット
uspto-grants-2006_01
特許番号
US06992087B2

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