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 1661073노트

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HRID 1661073 반응식
[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

참가 물질

6

반응물 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]

생성물 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 hydrochloride수율 15.4%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
70 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-36c345e863d84a0499163804e437e8b9
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030322B2

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