Sodium Iodide → 4-{[(Benzo[2,1,3]thiadiazol-4-yl)methyl]-isobutyl-amino}-piperidine-1-carboxylic acid tert-butyl ester

HRID 2111899

반응식

HRID 2111899 반응식
Br[CH2:2][C:3]1[C:11]2[C:7](=[N:8][S:9][N:10]=2)[CH:6]=[CH:5][CH:4]=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([NH:25][CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:12]([O:16][C:17]([N:19]1[CH2:20][CH2:21][CH:22]([N:25]([CH2:2][C:3]2[C:11]3[C:7](=[N:8][S:9][N:10]=3)[CH:6]=[CH:5][CH:4]=2)[CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:23][CH2:24]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

참가 물질

7

반응물 5

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 27762864-(Bromomethyl)-2,1,3-benzothiadiazoleHCID 153806991,1-Dimethylethyl 4-[(2-methylpropyl)amino]-1-piperidinecarboxylate

생성물 1

HCID 685746814-{[(Benzo[2,1,3]thiadiazol-4-yl)methyl]-isobutyl-amino}-piperidine-1-carboxylic acid tert-butyl ester수율 91.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
85 °C

실험 절차

4-Bromomethyl-benzo[2,1,3]thiadiazole (0.94 g, 4.12 mmol) is added to a stirred solution of 4-isobutylamino-piperidine-1-carboxylic acid tert-butyl ester (1.01 g, 3.95 mmol), potassium carbonate (0.66 g, 4.76 mmol), sodium iodide (0.18 g, 1.21 mmol), and anhydrous dimethylformamide (15 ml). The reaction is heated to 85° C. under nitrogen for 3 h. The reaction is poured into saturated sodium bicarbonate (100 ml) and extracted with ethyl acetate (100 ml×3). The ethyl acetate is dried over sodium sulfate and then the sodium sulfate is filtered off. The crude product is concentrated on a rotary evaporator and purified by flash chromatography on silica gel eluting with 10% ethyl acetate/hexanes to yield (1.46 g, 91%) of 4-{[(benzo[2,1,3]thiadiazol-4-yl)methyl]-isobutyl-amino}-piperidine-1-carboxylic acid tert-butyl ester: mass spectrum (ion spray): m/z=405.2 (M+1): 1H NMR (CDCl3): δ=7.86 (1H, d), 7.76-7.74 (1H, m), 7.60-7.56 (1H, m), 4.19 (2H, s), 4.12 (2H, br s), 2.68-2.54 (3H, m), 2.35 (2H, d), 1.83-1.79 (2H, m), 1.71-1.61 (1H, m), 1.54-1.46 (2H, m), 1.44 (9H, s), 0.87 (6H, d).

후처리

  1. extractionextracted with ethyl acetate (100 ml×3)
  2. dry with materialThe ethyl acetate is dried over sodium sulfate
  3. filtrationthe sodium sulfate is filtered off
  4. concentrationThe crude product is concentrated on a rotary evaporator
  5. custompurified by flash chromatography on silica gel eluting with 10% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-2f77e32aadf04b729e40a80a4d0b4e02
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07521462B2

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