Triphenylphosphine → morpholino(5-(3-(piperidin-1-yl)propoxy)-1H-indol-2-yl)methanone

HRID 901085

반응식

HRID 901085 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[O:12])=[CH:5]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:38]1([CH2:44][CH2:45][CH2:46]O)[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>C1COCC1>[N:13]1([C:11]([C:6]2[NH:7][C:8]3[C:4]([CH:5]=2)=[CH:3][C:2]([O:1][CH2:46][CH2:45][CH2:44][N:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)=[CH:10][CH:9]=3)=[O:12])[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 66032Piperidine-1-propanolHCID 44185244(5-hydroxy-1H-indol-2-yl)-morpholin-4-yl-methanone

생성물 1

HCID 11603156morpholino(5-(3-(piperidin-1-yl)propoxy)-1H-indol-2-yl)methanone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 246 mg (1 mmol) (5-hydroxy-1H-indol-2-yl)-morpholin-4-yl-methanone, 1 g (ca. 3 mmol) polymerbound triphenylphospine (Fluka), 179 mg (1.25 mmol) piperidinepropanol and 461 mg (2 mmol) di-tert.-butyl azadicarboxylate in 20 ml THF was stirred for a prolonged period of time at room temperature. The mixture was filtered through a pad of silica and washed with 30 ml THF. The mixture was evaporated to dryness and purified on silica eluting with a gradient of DCM/2N NH3 in methanol 98/2 to DCM/2N NH3 in methanol 9/1. The product fractions were evaporated and the residue was titurated with diethyl ether to yield after drying at 40° C. under vacuum 47 mg (13%) of the title compound as white solid. MS (m/e): 372.4 (MH+, 100%).

후처리

  1. filtrationThe mixture was filtered through a pad of silica
  2. washwashed with 30 ml THF
  3. customThe mixture was evaporated to dryness
  4. custompurified on silica eluting with a gradient of DCM/2N NH3 in methanol 98/2 to DCM/2N NH3 in methanol 9/1
  5. customThe product fractions were evaporated
  6. customto yield
  7. dry with materialafter drying at 40° C. under vacuum 47 mg (13%) of the title compound as white solid

출처 및 근거

ORD 기록
ord-a469e94487064f219429eef4992a5248
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361682B2

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