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

HRID 2040830ノート

反応式

HRID 2040830 の反応式
[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

参加物

8

反応物 5

HCID 757711-Hydroxybenzotriazole2 回HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2 回HCID 594979194-Benzyloxy-3-ethyl-5-methyl-benzoic acidHCID 670269622,2-Diethoxy-2-(2-isobutyl-6-methyl-pyridin-4-yl)-ethylamine dihydrochloride

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7bb0d3968d0d4ad7b1e78ddf434371a0
出典データセット
uspto-grants-2013_11
特許番号
US08580824B2

反応ノート

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