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Benzylamine → Ammonium Hydroxide

HRID 2243661
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HRID 2243661 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([S:29][CH3:30])[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=3[CH3:28])[C:22](O)=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:31].[CH2:32]([NH2:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>C(Cl)Cl>[NH4+:9].[OH-:23].[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([S:29][CH3:30])[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=3[CH3:28])[C:22]([NH:39][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:31]
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참가 물질

7

반응물 4

HCID 7504BenzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 119506223-[8-(2,6-Difluorophenyl)-2-(methylthio)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methylbenzoic acid

생성물 2

HCID 14923Ammonium Hydroxide
HCID 11950097
3-[8-(2,6-Difluorophenyl)-2-(methylthio)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-(phenylmethyl)benzamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

The compound 3-[8-(2,6-difluorophenyl)-2-(methylthio)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methylbenzoic acid (0.597 g, 1.35 mmol), benzyl amine (0.445 mL, 4.0 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.311 g, 1.62 mmol), 1-hydroxybenzotriazole hydrate (0.219 g, 1.62 mmol), were dissolved in CH2Cl2 (50 mL) and stirred under argon at room temperature for 16 h. The solvent was pumped off in vacuo. The reaction mixture was partitioned between ethyl acetate and water. The organic phase washed 3× with water, 1× brine, dried over anhydrous Na2SO4, filtered and evaporated. The crude product was flash chromatographed on silica gel (25 g) eluted with a gradient of 6:1:0.1, CH2Cl2:isopropanol:NH4OH to give the title compound. Crystallization from CH2Cl2/hexane gave the title compound as a white crystalline solid. m.p. (dec)154-159° C.; LC-MS m/z 532 (M+H)+, 2.24 min (ret. time).

후처리

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic phase washed 3× with water, 1× brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customchromatographed on silica gel (25 g)
  7. washeluted with a gradient of 6:1:0.1, CH2Cl2

출처 및 근거

ORD 기록
ord-5776bceccbd148a89dffac2523d22a89
출처 데이터셋
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07674789B2

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