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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
ノート
印刷プレビュー

反応式

HRID 1717408 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

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

生成物 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
収率 40%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-766f8b57143d42168b1737b711c22d72
出典データセット
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07803822B2

反応ノート

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