1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Tert-butyl 3-[(2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-benzoyl)-ethyl-amino]-propionate

HRID 604062ノート

反応式

HRID 604062 の反応式
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][N:7]([CH2:15][C:16]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21]C=1C(O)=O)[C:8]1[N:13]=[CH:12][C:11]([Br:14])=[CH:10][N:9]=1.[CH2:38]([NH:40][CH2:41][CH2:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH3:39].[OH2:50].O.ON1[C:57]2C=CC=C[C:56]=2N=N1.Cl.C(N=C=NCCCN(C)C)C>O1CCCC1.C(OCC)(=O)C.O.C(N(CC)CC)C>[F:37][C:2]([F:1])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][N:7]([CH2:15][C:16]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:39]=1[C:38]([N:40]([CH2:56][CH3:57])[CH2:41][CH2:42][C:43]([O:45][C:46]([CH3:48])([CH3:47])[CH3:49])=[O:44])=[O:50])[C:8]1[N:13]=[CH:12][C:11]([Br:14])=[CH:10][N:9]=1

参加物

9

反応物 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 20566209Tert-butyl 3-(ethylamino)propanoateHCID 666034961-Hydroxybenzotriazole dihydrateHCID 86626801HCID 86626801、化合物

生成物 1

HCID 86626819Tert-butyl 3-[(2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-benzoyl)-ethyl-amino]-propionate収率 98.6%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2-{[(3,5-Bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-benzoic acid (250 mg) is dissolved in tetrahydrofuran (5 ml), and thereto are added tert-butyl 3-ethylamino-propionate (103 mg), 1-hydroxybenzotriazole dihydrate (81 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (114 mg) and triethylamine (83 μl), and the mixture is stirred at room temperature overnight. To the reaction solution are added water and ethyl acetate, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=19:1→4:1) to give tert-butyl 3-[(2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-benzoyl)-ethyl-amino]-propionate (310 mg). MS (m/z): 757/759 [M+H]+

後処理

  1. customthe mixture is separated
  2. washthe organic layer is washed with a saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=19:1→4:1)

出典と根拠

ORDレコード
ord-e766a74ffd3b464fb001bf275318aac2
出典データセット
uspto-grants-2011_03
特許番号
US07906517B2

反応ノート

読み込み中…