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 604062노트

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HRID 604062 반응식
[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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

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]+

후처리

  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)

출처 및 근거

ORD 기록
ord-e766a74ffd3b464fb001bf275318aac2
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906517B2

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