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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Triethylamine → (E)-3-((7-chloro-3-(3-morpholino-3-oxoprop-1-enyl)imidazo[1,2-a]pyridin-2-yl)methyl)-1-cyclopropyl-1H-imidazo[4,5-c]pyridin-2(3H)-one

HRID 80634
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HRID 80634 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8](I)=[C:9]([CH2:11][N:12]3[C:16]4[CH:17]=[N:18][CH:19]=[CH:20][C:15]=4[N:14]([CH:21]4[CH2:23][CH2:22]4)[C:13]3=[O:24])[N:10]=[C:4]2[CH:3]=1.ClC1C=CN=C(N)C=1.CCN(CC)CC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:60]1[CH2:65][CH2:64][N:63]([C:66](=[O:69])[CH:67]=[CH2:68])[CH2:62][CH2:61]1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8](/[CH:68]=[CH:67]/[C:66]([N:63]3[CH2:64][CH2:65][O:60][CH2:61][CH2:62]3)=[O:69])=[C:9]([CH2:11][N:12]3[C:16]4[CH:17]=[N:18][CH:19]=[CH:20][C:15]=4[N:14]([CH:21]4[CH2:23][CH2:22]4)[C:13]3=[O:24])[N:10]=[C:4]2[CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 98723AcryloylmorpholineHCID 5818662-Amino-4-chloropyridineHCID 679876583-((7-chloro-3-iodoimidazo[1,2-a]pyridin-2-yl)methyl)-1-cyclopropyl-1H-imidazo[4,5-c]pyridin-2(3H)-one

생성물 1

HCID 57410366
(E)-3-((7-chloro-3-(3-morpholino-3-oxoprop-1-enyl)imidazo[1,2-a]pyridin-2-yl)methyl)-1-cyclopropyl-1H-imidazo[4,5-c]pyridin-2(3H)-one
수율 92%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

실험 절차

A solution of 3-((7-chloro-3-iodoimidazo[1,2-a]pyridin-2-yl)methyl)-1-cyclopropyl-1H-imidazo[4,5-c]pyridin-2(3H)-one 12-a (prepared following the 3-step synthesis used for 7-b, using 4-chloro-2-aminopyridine instead of 2-aminopyridine in step 1) and Et3N (2.218 mL, 8 eq) in DMF (30 mL) was degassed with nitrogen for fifteen minutes. Then palladium acetate (45 mg, 0.1 eq), triphenylphosphine (173 mg, 0.33 eq) and 1-morpholinoprop-2-en-1-one (2.516 mL, 10 eq) were added and stirring in a closed vessel was allowed at 80° C. during two hours. After cooling the mixture was quenched with ice water. After one hour stirring the precipitate was filtered off and dried in vacuo. The solid was purified over silica with dichloromethane/methanol-NH3 98/2 as eluent to provide the target compound P24 in 92% yield (884 mg). m/z=479 (M+H)+;

후처리

  1. customthe 3-step synthesis
  2. customwas degassed with nitrogen for fifteen minutes
  3. temperatureAfter cooling the mixture
  4. customwas quenched with ice water
  5. stirringAfter one hour stirring the precipitate
  6. filtrationwas filtered off
  7. customdried in vacuo
  8. customThe solid was purified over silica with dichloromethane/methanol-NH3 98/2 as eluent
  9. customto provide the target compound P24 in 92% yield (884 mg)

출처 및 근거

ORD 기록
ord-0819504441b64db8a15f38ec8030cda9
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846672B2

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