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Nitrogen → Ammonia

HRID 1524194
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HRID 1524194 반응식
Br[C:2]1[N:7]=[C:6]2[N:8]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([Cl:17])[CH:12]=3)[CH:9]=[N:10][C:5]2=[CH:4][CH:3]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[N:64]#N.N[CH:67]1[CH2:72][CH2:71][CH2:70][CH:69]([OH:73])[CH2:68]1.CC(C)([O-])C.[Na+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[NH3:7].[Cl:17][C:13]1[CH:12]=[C:11]([N:8]2[C:6]3=[N:7][C:2]([CH:70]4[CH2:71][CH2:72][CH2:67][CH2:68][C:69]4([NH2:64])[OH:73])=[CH:3][CH:4]=[C:5]3[N:10]=[CH:9]2)[CH:16]=[CH:15][N:14]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 947NitrogenHCID 634876Binap, (A+-)-HCID 112404593-AminocyclohexanolHCID 23676156Sodium t-butoxideHCID 866518705-bromo-3-(2-chloro-pyridin-4-yl)-3-H-imidazo[4,5-b]pyridine2회

생성물 2

HCID 222Ammonia
HCID 131733125
3-(2-chloro-pryidin-4-yl)-3H-imidazo[4,5-b]pyridine-5-yl aminocyclohexanol

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매2회

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온도
85 °C

실험 절차

5-Bromo-3-(2-chloro-pyridin-4-yl)-3-H-imidazo[4,5-b]pyridine (Intermediate A)(1 eq, 0.323 mmol, 100 mg), BINAP (0.025 mmol, 40 mg) and Pd2(dba)3 (0.0125 mmol, 25 mg) are suspended in dioxane under an inert atmosphere of N2 and heated to 85° C. In a separate flask (1SR,3SR)-3-aminocyclohexanol (2 eq, 0.647 mmol, 83 mg) and sodium tertbutoxide (2.5 eq, 0.809 mmol, 77 mg) is dissolved in dioxane and warmed to 50° C. Once at temperature mixture is added to the reaction mixture and heated for 2 hours. After cooling to room temperature, the mixture is purified by chromatography on silica eluting with 98:2 DCM: 2M ammonia in MeOH to afford the title compound which is used in the next step without further purification; [M+H]+ 310.

후처리

  1. temperaturewarmed to 50° C
  2. additionOnce at temperature mixture is added to the reaction mixture
  3. temperatureheated for 2 hours
  4. temperatureAfter cooling to room temperature
  5. customthe mixture is purified by chromatography on silica eluting with 98:2 DCM

출처 및 근거

ORD 기록
ord-b1f7c538022b4ae696958ca6023e5bce
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09079897B2

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