1-Hydroxybenzotriazole → N-(4'-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1'-biphenyl-3-yl)-3-fur-3-ylbenzamide

HRID 2114137노트

반응식

HRID 2114137 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:21])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH:16][CH2:17][CH:18]3[CH2:20][CH2:19]3)=[O:15])=[CH:10][CH:9]=2)[CH:7]=1.[O:22]1[CH:26]=[CH:25][C:24]([C:27]2[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=2)[C:30](O)=[O:31])=[CH:23]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:18]1([CH2:17][NH:16][C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:6]3[C:5]([CH3:21])=[CH:4][CH:3]=[C:2]([NH:1][C:30](=[O:31])[C:29]4[CH:33]=[CH:34][CH:35]=[C:27]([C:24]5[CH:25]=[CH:26][O:22][CH:23]=5)[CH:28]=4)[CH:7]=3)=[CH:9][CH:10]=2)=[O:15])[CH2:20][CH2:19]1

참가 물질

7

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 113004885'-amino-N-(cyclopropylmethyl)-2'-methyl-1,1'-biphenyl-4-carboxamideHCID 189451333-(Furan-3-yl)benzoic acid

생성물 1

HCID 44578806N-(4'-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1'-biphenyl-3-yl)-3-fur-3-ylbenzamide수율 79.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

5′-Amino-N-(cyclopropylmethyl)-2′-methyl-1,1′-biphenyl-4-carboxamide (48 mg, 0.17 mmol), 3-fur-3-ylbenzoic acid (32 mg, 0.17 mmol), HATU (65 mg, 0.17 mmol), HOBT (23 mg, 0.17 mmol) and DIPEA (88 μl) were stirred in DMF (1.5 ml) for 18 h at room temperature. The reaction was partitioned between ethyl acetate (100 ml) and hydrochloric acid (0.5M, 20 ml), the organic phase washed with aqueous sodium hydrogen carbonate (saturated) and dried (magnesium sulphate). The solvent was evaporated under vacuum to give N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)-3-fur-3-ylbenzamide (61 mg, 79%). NMR; δH [2H6]—DMSO 10.16,(1H, s), 8.35,(1H, t), 8.22,(1H, s), 7-89,(2H, d), 7.79,(2H, t), 7.69-7.65,(2H, m), 7.56,(1H, s), 7.45,(1H, t), 7.35,(2H, d), 7.19,(1H, d), 6.85,(1H, d), 6.49,(1H, m), 3.17,(2H, t), 2.18,(3H, s), 1.04,(1H, m), 0.42,(2H, m), 0.22,(2H, m). LCMS: retention time 3.75 min, MH+451.

후처리

  1. customThe reaction was partitioned between ethyl acetate (100 ml) and hydrochloric acid (0.5M, 20 ml)
  2. washthe organic phase washed with aqueous sodium hydrogen carbonate (saturated)
  3. dry with materialdried (magnesium sulphate)
  4. customThe solvent was evaporated under vacuum

출처 및 근거

ORD 기록
ord-da0eb9fec6de4ac3b9754145e28aaf3b
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432289B2

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