Trifluoroacetic acid → (+/-)-trans-N-[(5-methyl-4,5,6,7-tetrahydrothiazolo-[5,4-c]pyridin-2-yl)carbonyl]-1,2-cyclohexanediamine trifluoroacetate

HRID 459468노트

반응식

HRID 459468 반응식
C(O[C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH2:15])=[O:7])(C)(C)C.[CH3:16][N:17]1[CH2:22][CH2:21][C:20]2[N:23]=[C:24](C([O-])=O)[S:25][C:19]=2[CH2:18]1.[Li+].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[F:53][C:54]([F:59])([F:58])[C:55]([OH:57])=[O:56]>CN(C)C=O.ClCCl>[F:53][C:54]([F:59])([F:58])[C:55]([OH:57])=[O:56].[CH3:16][N:17]1[CH2:22][CH2:21][C:20]2[N:23]=[C:24]([C:6]([NH:8][C@@H:9]3[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]3[NH2:15])=[O:7])[S:25][C:19]=2[CH2:18]1

참가 물질

8

반응물 5

HCID 6422Trifluoroacetic acidHCID 1514390(1R,2R)-trans-N-Boc-1,2-cyclohexanediamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 23704331Lithium 5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate

생성물 1

HCID 18442875(+/-)-trans-N-[(5-methyl-4,5,6,7-tetrahydrothiazolo-[5,4-c]pyridin-2-yl)carbonyl]-1,2-cyclohexanediamine trifluoroacetate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

(±)-trans-N-tert-Butoxycarbonyl-1,2-cyclohexane-diamine (642 mg) was dissolved in N,N-dimethylformamide (20 ml), and to the solution lithium 5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate (795 mg), 1-hydroxybenzotriazole monohydrate (46 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.30 g) were added, and the mixture was stirred overnight at room temperature. After the reaction mixture was concentrated under reduced pressure, and dichloromethane and water were added to the residue, the organic layer was taken out and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (dichloromethane:methanol=100:3) to obtain a pale yellow foamy substance. This substance was dissolved in dichloromethane (5 ml), and trifluoroacetic acid (30 ml) was added, and the mixture was stirred at room temperature for 1 minute. The reaction mixture was concentrated under reduced-pressure to obtain the title compound (731 mg) as a pale brown foamy substance.

후처리

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure, and dichloromethane and water
  2. additionwere added to the residue
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (dichloromethane:methanol=100:3)
  6. customto obtain a pale yellow foamy substance
  7. stirringthe mixture was stirred at room temperature for 1 minute
  8. concentrationThe reaction mixture was concentrated under reduced-pressure

출처 및 근거

ORD 기록
ord-41142c61bec2417d98cc07b2eff8f53b
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07192968B2

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