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Dichloromethane → HCID 53379558, 화합물

HRID 1771560
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HRID 1771560 반응식
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:14][CH:13]3[O:15][CH:10]([CH2:11][CH2:12]3)[CH2:9]2)[CH:5]=[CH:4][N:3]=1.[CH2:16]([NH:18][C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25](B2OC(C)(C)C(C)(C)O2)=[CH:24][CH:23]=1)=[O:20])[CH3:17].C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.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]>[CH:10]12[O:15][CH:13]([CH2:12][CH2:11]1)[CH2:14][N:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:25]3[CH:24]=[CH:23][C:22]([NH:21][C:19]([NH:18][CH2:16][CH3:17])=[O:20])=[CH:27][CH:26]=3)[N:7]=1)[CH2:9]2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 44119377N-Ethyl-N'-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ureaHCID 663715273-(2-Chloropyrimidin-4-yl)-8-oxa-3-azabicyclo[3,2,1]octane2회

생성물 1

HCID 53379558HCID 53379558, 화합물

시약·촉매·용매 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 18180031Water 1,2-dimethoxyethane용매

실험 절차

3-(2-chloropyrimidin-4-yl)-8-oxa-3-azabicyclo[3,2,1]octane (intermediate 24) (100 mg, 0.44 mmol) was stirred with 1-ethyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (141 mg, 0.48 mmol), Pd(dppf)Cl2:DCM (18 mg, 0.002) and Na2CO3(140 mg, 1.3 mmol) in DME:Water (4:1) for 30 minutes at 130° C. in microwave conditions. The reaction mixture was filtered through a celite545 cake and washed with methanol. The reaction mixture was concentrated in vacuo. The resulting oil was purified by prep HPLC at low pH to afford the title compound as a white solid. (20 mg, 13%)

후처리

  1. filtrationThe reaction mixture was filtered through a celite545 cake
  2. washwashed with methanol
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customThe resulting oil was purified by prep HPLC at low pH

출처 및 근거

ORD 기록
ord-768c6b4f279948de851cf04a36db32d5
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09249129B2

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