Diisopropylethylamine → HCID 58381304, 화합물

HRID 39416

반응식

HRID 39416 반응식
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([S:16][CH3:17])[C:4]=1[C:5]([OH:7])=O.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[O:51]1[C:55]2([CH2:60][CH2:59][O:58][CH2:57][CH:56]2[NH2:61])[O:54][CH2:53][CH2:52]1>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([S:16][CH3:17])[C:4]=1[C:5]([NH:61][CH:56]1[CH2:57][O:58][CH2:59][CH2:60][C:55]21[O:54][CH2:53][CH2:52][O:51]2)=[O:7]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58381253HCID 58381253, 화합물HCID 591979212-Methoxy-6-methylsulfanyl-4-trifluoromethyl-benzoic acid2회

생성물 1

HCID 58381304HCID 58381304, 화합물수율 75.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2-Methoxy-6-methylsulfanyl-4-trifluoromethyl-benzoic acid (intermediate A, 400 mg, 1.5 mmol) was dissolved in 10 mL dimethylformamide. N,N-Diisopropyl ethyl amine (505 mg, 3.9 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (571 mg, 1.5 mmol) were added. After 10 minutes of stirring at room temperature 1,4,8-trioxaspiro[4,5]decan-6-amine (CAS 1068523-26-1) (359 mg, 2.2 mmol) was added. The reaction mixture was stirred at room temperature overnight. The solvent was evaporated off. The residue was taken up in 2N sodium carbonate solution and ethyl acetate and was extracted three times with ethyl acetate. The combined organic phases were dried on sodium sulfate, filtered and evaporated. Purification of the residue by flash chromatography on silica gel (heptane/ethyl acetate/triethylamine 1:0:0→10:10:1) yielded 2-methoxy-6-methylsulfanyl-4-trifluoromethyl-N-(1,4,8-trioxa-spiro[4.5]dec-6-yl)-benzamide as a white solid (462 mg, 75%), MS: m/e=408.2 [(M+H)+].

후처리

  1. additionwas added
  2. customThe solvent was evaporated off
  3. extractionethyl acetate and was extracted three times with ethyl acetate
  4. customThe combined organic phases were dried on sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification of the residue by flash chromatography on silica gel (heptane/ethyl acetate/triethylamine 1:0:0→10:10:1)

출처 및 근거

ORD 기록
ord-be7be8ac29894dacb47f3756857fa5f6
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524909B2

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