Triethylamine → [3-(3-Chloromethyl-[1,2,4]oxadiazol-5-yl)-phenyl]-methanol

HRID 273127노트

반응식

HRID 273127 반응식
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O.[Cl:12][CH2:13][C:14]([NH:16]O)=[NH:15].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[Cl:12][CH2:13][C:14]1[N:16]=[C:6]([C:5]2[CH:4]=[C:3]([CH2:2][OH:1])[CH:11]=[CH:10][CH:9]=2)[O:8][N:15]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 185629Benzoic acid, 3-(hydroxymethyl)-HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178511097HCID 178511097, 화합물

생성물 1

HCID 67070834[3-(3-Chloromethyl-[1,2,4]oxadiazol-5-yl)-phenyl]-methanol수율 25%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

3-Hydroxymethylbenzoic acid, described in Reed, G. A.; Dimmel, D. R.; Malcolm, E. W. J. Org. Chem. 1993, 58 (23), 6372-6376, (175 mg, 1.15 mmol), 2-chloro-N-hydroxy-acetamidine (125 mg, 1.15 mmol) and HBTU was dissolved in anhydrous DMF (4 ml). Triethylamine (0.48 ml, 3.5 mmol) was added and the reaction was stirred at ambient temperature over night. The crude product was partitioned between dichloromethane and NaHCO3 (aq), the organic phase was dried (MgSO4) and the dichloromethane was removed in vacuo. The resulting DMF-solution was heated at 120° C. over night. The reaction mixture was concentrated in vacuo and the title compound (64 mg, 25%) was isolated by flash chromatography using 25-50% ethyl acetate in heptane. 1H NMR (CDCl3), δ (ppm): 8.15 (s, 1H), 8.06 (d, 1H), 7.62 (d, 1H), 7.53 (t, 1H); 4.80 (d, 2H), 4.66 (s, 1H); 1.99 (br. t, 1H).

후처리

  1. customThe crude product was partitioned between dichloromethane and NaHCO3 (aq)
  2. dry with materialthe organic phase was dried (MgSO4)
  3. customthe dichloromethane was removed in vacuo
  4. temperatureThe resulting DMF-solution was heated at 120° C. over night
  5. concentrationThe reaction mixture was concentrated in vacuo

출처 및 근거

ORD 기록
ord-f7859a9a437b423694b0b5d78516218a
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456200B2

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