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Sodium Carbonate → (S)-tert-butyl 1-(6-(4-(benzyloxy)pyrimidin-2-yl)quinolin-4-yl)piperidin-3-ylcarbamate

HRID 1028060
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HRID 1028060 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][CH:13]=[C:12]3[N:19]2[CH2:24][CH2:23][CH2:22][C@H:21]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:20]2)O1.[CH2:34]([O:41][C:42]1[CH:47]=[CH:46][N:45]=[C:44](Cl)[N:43]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.COCCOC>[CH2:34]([O:41][C:42]1[CH:47]=[CH:46][N:45]=[C:44]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][CH:13]=[C:12]3[N:19]2[CH2:24][CH2:23][CH2:22][C@H:21]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[CH2:20]2)[N:43]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1
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참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 151332374-(Benzyloxy)-2-chloropyrimidineHCID 67316377(S)-tert-butyl 1-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-4-yl)piperidin-3-ylcarbamate

생성물 1

HCID 67338681(S)-tert-butyl 1-(6-(4-(benzyloxy)pyrimidin-2-yl)quinolin-4-yl)piperidin-3-ylcarbamate수율 88%

시약·촉매·용매 2

HCID 178418807
HCID 178418807, 화합물
촉매
HCID 80711,2-Dimethoxyethane용매

실험 절차

To a mixture of (S)-tert-butyl 1-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-4-yl)piperidin-3-ylcarbamate (1.0 equiv.), 4-(benzyloxy)-2-chloropyrimidine (2.0 equiv.) and Pd(dppf)Cl2-DCM (0.15 equiv) in a 20 ml microwave vial, DME and 2M Na2CO3 were added (1.0 M). The vial was submitted to 125° C. for 20 min in microwave. The resulting mixture was partitioned between EtOAc and H2O. Upon separation, the organic layer was washed with NaCl(sat.), dried over Na2SO4, concentrated and purified by reverse-phase HPLC to yield (S)-tert-butyl 1-(6-(4-(benzyloxy)pyrimidin-2-yl)quinolin-4-yl)piperidin-3-ylcarbamate (88%). LC/MS=512.1 (M+H), LC=3.40 min.

후처리

  1. additionwere added (1.0 M)
  2. customThe resulting mixture was partitioned between EtOAc and H2O
  3. customUpon separation
  4. washthe organic layer was washed with NaCl(sat.)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. custompurified by reverse-phase HPLC

출처 및 근거

ORD 기록
ord-0b71be8b6bec49f38e28495a9ce11354
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08735424B2

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