Citric Acid → HCID 57572194, 화합물

HRID 602135노트

반응식

HRID 602135 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10](NC)=[C:11]([CH3:13])[N:12]=2)=[CH:4][CH:3]=1.[C:16]([O:20][C:21]([N:23]1[CH2:31][CH2:30][CH2:29][CH:25]([C:26](O)=[O:27])[CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].O.O[N:34]1[C:38]2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.CN1CCOCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[C:16]([O:20][C:21]([N:23]1[CH2:31][CH2:30][CH2:29][CH:25]([C:26]([NH:34][CH2:38][C:10]2[S:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[N:12][C:11]=2[CH3:13])=[O:27])[CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]

참가 물질

8

반응물 6

HCID 311Citric AcidHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27356471-((Tert-butoxy)carbonyl)piperidine-3-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 672668402-(4-Chlorophenyl)-4-methylthiazol-5-yl methylamine

생성물 1

HCID 57572194HCID 57572194, 화합물수율 101.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2-(4-Chlorophenyl)-4-methylthiazol-5-yl methylamine (477 mg, 2.00 mmol), 1-tert-butoxycarbonyl nipecotic acid (459 mg, 2.00 mmol) and 1-hydroxybenzotriazole monohydrate (368 mg, 2.40 mmol) were dissolved in N,N-dimethylformamide (10 mL). While this mixture was chilled in an ice bath, 3-(3-dimethylaminopropyl)-1-ethylcarbodiimide hydrochloride (460 mg, 2.40 mmol) and N-methylmorpholine (0.484 mL, 4.40 mmol) were added. The mixture was then stirred at room temperature for 6 hours. Subsequently, 5% aqueous citric acid was added and the mixture was extracted with ethyl acetate. The extract washed sequentially with a saturated aqueous sodium bicarbonate solution and brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the residue by silica gel column chromatography (hexane:ethyl acetate=5:1->1:1) gave 916 mg (100%) of the desired compound as a colorless powder.

후처리

  1. temperatureWhile this mixture was chilled in an ice bath
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract washed sequentially with a saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialby drying over magnesium sulfate and evaporation of the solvent
  5. customPurification of the residue by silica gel column chromatography (hexane:ethyl acetate=5:1->1:1)

출처 및 근거

ORD 기록
ord-97e81394ce7748fda324e712d980606a
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902367B2

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