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Acetic Acid → N-(2-{[4-(2,4-dichlorophenyl)-5-(morpholin-4-ylmethyl)pyrimidin-2-yl]amino)ethyl)(tert-butoxy)carboxamide

HRID 1825537
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HRID 1825537 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14](C=O)=[CH:13][N:12]=[C:11]([NH:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[N:10]=1.[C:28]([BH3-])#[N:29].[Na+].C(O)(=O)C.O.[CH2:37]1[CH2:41][O:40][CH2:39][CH2:38]1>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([CH2:28][N:29]2[CH2:37][CH2:41][O:40][CH2:39][CH2:38]2)=[CH:13][N:12]=[C:11]([NH:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:25])[CH3:26])=[O:22])[N:10]=1
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참가 물질

6

반응물 5

HCID 176Acetic AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 22142985n-(2-{[4-(2,4-Dichlorophenyl)-5-formylpyrimidin-2-yl]amino}ethyl)(tert-butoxy)-carboxamide

생성물 1

HCID 22142523N-(2-{[4-(2,4-dichlorophenyl)-5-(morpholin-4-ylmethyl)pyrimidin-2-yl]amino)ethyl)(tert-butoxy)carboxamide

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온도
70 °C

실험 절차

N-(2-{[4-(2,4-dichlorophenyl)-5-formylpyrimidin-2-yl]amino}ethyl)(tert-butoxy)carboxamide (50 mg, 0.121 mmol) was dissolved in 5 mL of THF, 242 μL of sodium cyanoborohydride (1 M in THF) and 5 μL of glacial acetic acid added and the mixture was heated to 70° C. for 18 h. Following slow addition of 1 mL of water to decompose excess reagent, the mixture was partitioned between ethyl acetate and saturated citric acid solution. The organic layer was discarded, and aqueous layer was carefully basified with sodium hydoxide to PH 9, then extracted with ethyl acetate twice. The combined organic layers was dried (sodium sulfate), concentrated, and purified by chromatography (selica gel, 10% methanol/methylene chloride) to afford N-(2-{[4-(2,4-dichlorophenyl)-5-(morpholin-4-ylmethyl)pyrimidin-2-yl]amino}ethyl)(tert-butoxy)carboxamide, 30 mg (52%).

후처리

  1. customthe mixture was partitioned between ethyl acetate and saturated citric acid solution
  2. extractionextracted with ethyl acetate twice
  3. dry with materialThe combined organic layers was dried (sodium sulfate)
  4. concentrationconcentrated
  5. custompurified by chromatography (selica gel, 10% methanol/methylene chloride)

출처 및 근거

ORD 기록
ord-945f4d0ebd1b4907bb8dffccb6614b79
출처 데이터셋
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07045519B2

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