1-Hydroxybenzotriazole → 4-benzyloxy-N-[2,2-diethoxy-2-(2-isobutyl-6-methyl-pyridin-4-yl)-ethyl]-3-ethyl-5-methyl-benzamide

HRID 2040830노트

반응식

HRID 2040830 반응식
[CH2:1]([O:8][C:9]1[C:17]([CH3:18])=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][C:10]=1[CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.Cl.[CH2:54]([O:56][C:57]([O:71][CH2:72][CH3:73])([C:60]1[CH:65]=[C:64]([CH3:66])[N:63]=[C:62]([CH2:67][CH:68]([CH3:70])[CH3:69])[CH:61]=1)[CH2:58][NH2:59])[CH3:55]>CN(C=O)C.CC(=O)OCC>[CH2:1]([O:8][C:9]1[C:17]([CH3:18])=[CH:16][C:12]([C:13]([NH:59][CH2:58][C:57]([O:71][CH2:72][CH3:73])([O:56][CH2:54][CH3:55])[C:60]2[CH:65]=[C:64]([CH3:66])[N:63]=[C:62]([CH2:67][CH:68]([CH3:69])[CH3:70])[CH:61]=2)=[O:15])=[CH:11][C:10]=1[CH2:19][CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 5

HCID 757711-Hydroxybenzotriazole2회HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2회HCID 594979194-Benzyloxy-3-ethyl-5-methyl-benzoic acidHCID 670269622,2-Diethoxy-2-(2-isobutyl-6-methyl-pyridin-4-yl)-ethylamine dihydrochloride

생성물 1

HCID 685531514-benzyloxy-N-[2,2-diethoxy-2-(2-isobutyl-6-methyl-pyridin-4-yl)-ethyl]-3-ethyl-5-methyl-benzamide수율 60.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-benzyloxy-3-ethyl-5-methylbenzoic acid (115 mg, 0.425 mmol) in DMF (1.5 mL), EDC HCl (46 mg, 0.467 mmol) followed by HOBT (63 mg, 0.467 mmol) is added. The mixture is stirred at rt for 15 min before DIPEA (219 mg, 1.70 mmol) and a solution of 2,2-diethoxy-2-(2-isobutyl-6-methyl-pyridin-4-yl)-ethylamine dihydrochloride (150 mg, 0.425 mmol) in DMF (0.5 mL) is added. The mixture is stirred at rt for 4.5 h before another portion of EDC HCl (20 mg) and HOBT (30 mg) is added. Stirring is continued at rt for 16 h. The mixture is diluted with EA (30 mL), washed with sat. aq. NaHCO3 solution (15 mL), water (15 mL) and brine (15 mL), dried over Na2SO4, filtered and concentrated. The crude product is purified on prep. TLC with heptane:EA 1:1 to give 4-benzyloxy-N-[2,2-diethoxy-2-(2-isobutyl-6-methyl-pyridin-4-yl)-ethyl]-3-ethyl-5-methyl-benzamide (137 mg) as a pale yellow wax; LC-MS: tR=1.13, [M+1]+=533.15.

후처리

  1. additionis added
  2. additionis added
  3. washwashed with sat. aq. NaHCO3 solution (15 mL), water (15 mL) and brine (15 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified on prep

출처 및 근거

ORD 기록
ord-7bb0d3968d0d4ad7b1e78ddf434371a0
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580824B2

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