N-(2-(p-bromophenoxy)ethyl)pyrrolidine → HCID 59589976, 화합물

HRID 1472874

반응식

HRID 1472874 반응식
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[N:16]4[N:17]=[C:18]([NH2:20])[N:19]=[C:15]4[CH:14]=[CH:13][C:12]=3[O:21][CH3:22])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.Br[C:24]1[CH:37]=[CH:36][C:27]([O:28][CH2:29][CH2:30][N:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)=[CH:26][CH:25]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC(C)([O-])C.[Na+]>CC(N(C)C)=O.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].O1CCOCC1>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[N:16]4[N:17]=[C:18]([NH:20][C:24]5[CH:25]=[CH:26][C:27]([O:28][CH2:29][CH2:30][N:31]6[CH2:32][CH2:33][CH2:34][CH2:35]6)=[CH:36][CH:37]=5)[N:19]=[C:15]4[CH:14]=[CH:13][C:12]=3[O:21][CH3:22])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

참가 물질

8

반응물 4

HCID 70657N-(2-(p-bromophenoxy)ethyl)pyrrolidineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 595896845-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-6-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

생성물 1

HCID 59589976HCID 59589976, 화합물

시약·촉매·용매 3

HCID 31374Dimethylacetamide촉매HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매HCID 312751,4-Dioxane용매

반응 조건

온도
150 °C

실험 절차

In a microwave vial, 5-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-6-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (0.05 g, 0.17 mmol), 1-[2-(4-bromophenoxy)ethyl]-pyrrolidine (0.068 g, 0.251 mmol), bis(dibenzylideneacetone)palladium (0.005 g, 0.008 mmol), Xantphos (0.01 g, 0.017 mmol) and sodium tert-butoxide (0.033 g, 0.335 mmol) were added successively. Dioxane (1.2 mL) and dimethylacetamide (2 drops) were added and the vial was sealed and heated in the microwave (150° C., 10 min). The crude was purified using an SCX cartridge, by washing with methanol and releasing the compound with 2M ammonia in methanol. After concentration under reduced pressure, the crude was purified by preparatory LCMS. LCMS Method: 2: RT: 2.52 min, MI: 488 [M+1].

후처리

  1. customthe vial was sealed
  2. customThe crude was purified
  3. washby washing with methanol
  4. concentrationAfter concentration under reduced pressure
  5. customthe crude was purified by preparatory LCMS

출처 및 근거

ORD 기록
ord-5c5e2e70bf91492fbd9b29cdbe57ac50
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012633B2

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