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Acetic Acid → N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-({[(1-trityl-1H-imidazol-2-yl)methyl]amino}methyl)-1H-1,2,3-triazole-4-carboxamide

HRID 1717408
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HRID 1717408 반응식
[NH2:1][CH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH:16][CH2:17][CH3:18])=[O:15])=[CH:10][CH:9]=2)[N:6]=[N:5][C:4]=1[C:19]([NH:21][CH:22]1[CH2:24][CH2:23]1)=[O:20].[C:25]([N:44]1[CH:48]=[CH:47][N:46]=[C:45]1[CH:49]=O)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClC(Cl)C>[CH:22]1([NH:21][C:19]([C:4]2[N:5]=[N:6][N:7]([C:8]3[CH:9]=[CH:10][C:11]([C:14]([NH:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:13]=3)[C:3]=2[CH2:2][NH:1][CH2:49][C:45]2[N:44]([C:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:48]=[CH:47][N:46]=2)=[O:20])[CH2:24][CH2:23]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 6182531-(triphenylmethyl)-1H-imidazole-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 57664928HCID 57664928, 화합물

생성물 1

HCID 57664825
N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-({[(1-trityl-1H-imidazol-2-yl)methyl]amino}methyl)-1H-1,2,3-triazole-4-carboxamide
수율 40%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

To a solution of 5-(aminomethyl)-N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamide (164 mg, 0.5 mmol) obtained in Example 1197 in dichloroethane (10 ml) were successively added 1-trityl-1H-imidazole-2-carbaldehyde (169 mg, 0.5 mmol), acetic acid (30 mg, 0.5 mmol) and sodium triacetoxyborohydride (138 mg, 0.65 mmol) at 0° C., and the mixture was stirred at room temperature for 48 hr. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution (5 ml) and, after partitioning, the organic layer was dried over magnesium sulfate and concentrated. The residue was purified by silica gel column (hexane/ethyl acetate=1/1 to ethyl acetate/methanol=4/1) to give the title compound as a colorless powder (130 mg, 40%).

후처리

  1. customat 0° C.
  2. customafter partitioning
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column (hexane/ethyl acetate=1/1 to ethyl acetate/methanol=4/1)

출처 및 근거

ORD 기록
ord-766f8b57143d42168b1737b711c22d72
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07803822B2

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