Sodium Iodide → 5-(5-(3-(5-chloro-6-methoxy-2,3-dihydrospiro[indene-1,3'-pyrrolidine]-1'-yl)propylthio)-4-methyl-4H-1,2,4-triazol-3-yl)-2,4-dimethylthiazole hydrochloride

HRID 1661073ノート

反応式

HRID 1661073 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[C:7]1([CH2:11][CH2:10][NH:9][CH2:8]1)[CH2:6][CH2:5]2.Cl[CH2:18][CH2:19][CH2:20][S:21][C:22]1[N:23]([CH3:34])[C:24]([C:27]2[S:31][C:30]([CH3:32])=[N:29][C:28]=2[CH3:33])=[N:25][N:26]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CN1C(=O)CCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[C:7]1([CH2:11][CH2:10][N:9]([CH2:18][CH2:19][CH2:20][S:21][C:22]3[N:23]([CH3:34])[C:24]([C:27]4[S:31][C:30]([CH3:32])=[N:29][C:28]=4[CH3:33])=[N:25][N:26]=3)[CH2:8]1)[CH2:6][CH2:5]2

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 446278985-(5-(3-chloropropylthio)-4-methyl-4H-1,2,4-triazol-3-yl)-2,4-dimethylthiazoleHCID 592339355-Chloro-6-methoxy-2,3-dihydrospiro[indene-1,3'-pyrrolidine]

生成物 1

HCID 674289485-(5-(3-(5-chloro-6-methoxy-2,3-dihydrospiro[indene-1,3'-pyrrolidine]-1'-yl)propylthio)-4-methyl-4H-1,2,4-triazol-3-yl)-2,4-dimethylthiazole hydrochloride収率 15.4%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
70 °C

実験手順

The mixture of 5-chloro-6-methoxy-2,3-dihydrospiro[indene-1,3′-pyrrolidine] (Prep19, 58 mg, 0.24 mmol), 5-(5-(3-chloropropylthio)-4-methyl-4H-1,2,4-triazol-3-yl)-2,4-dimethylthiazole (Prep28, 50 mg, 0.17 mmol), K2CO3 (68.5 mg, 0.50 mmol) and NaI (24.5 mg, 0.50 mmol) in NMP (1 ml) was warmed to 70° C., and stirred overnight. The mixture was extracted with EA (5 ml×2). The combined organic layers were washed with Sat. NaHCO3, brine and dried over Na2SO4. The organic layer was concentrated in vacuo to afford crude product. The crude was purified by P-TLC and P-HPLC and treated with a 1N solution of HCl in ether, then freeze-dried to afford title compound (10 mg, y=11.98%).

後処理

  1. extractionThe mixture was extracted with EA (5 ml×2)
  2. washThe combined organic layers were washed with Sat. NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. concentrationThe organic layer was concentrated in vacuo
  5. customto afford crude product
  6. customThe crude was purified by P-TLC and P-HPLC
  7. additiontreated with a 1N solution of HCl in ether
  8. customfreeze-dried

出典と根拠

ORDレコード
ord-36c345e863d84a0499163804e437e8b9
出典データセット
uspto-grants-2011_10
特許番号
US08030322B2

反応ノート

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