Chloroform → 7-{[(1-{[(2R)-3,8-Dioxo-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylen-2-yl]methyl}-4-piperidinyl)amino]methyl}-2,3-dihydro-1,4-benzodioxin-5-carbonitrile hydrochloride

HRID 1943228노트

반응식

HRID 1943228 반응식
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C@H:9]2[N:19]3[C:20]4[N:11]([C:12](=[O:22])[CH:13]=[CH:14][C:15]=4[N:16]=[CH:17][C:18]3=[O:21])[CH2:10]2)[CH2:4][CH2:3]1.[CH:23]([C:25]1[CH:26]=[C:27]([C:35]#[N:36])[C:28]2[O:33][CH2:32][CH2:31][O:30][C:29]=2[CH:34]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+].C(Cl)(Cl)[Cl:57]>CO>[ClH:57].[O:21]=[C:18]1[CH:17]=[N:16][C:15]2=[C:20]3[N:19]1[C@H:9]([CH2:8][N:5]1[CH2:6][CH2:7][CH:2]([NH:1][CH2:23][C:25]4[CH:26]=[C:27]([C:35]#[N:36])[C:28]5[O:33][CH2:32][CH2:31][O:30][C:29]=5[CH:34]=4)[CH2:3][CH2:4]1)[CH2:10][N:11]3[C:12](=[O:22])[CH:13]=[CH:14]2

참가 물질

7

반응물 5

HCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 57423114HCID 57423114, 화합물HCID 58200877(2R)-2-[(4-Amino-1-piperidinyl)methyl]-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylene-3,8-dione

생성물 1

HCID 685971587-{[(1-{[(2R)-3,8-Dioxo-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylen-2-yl]methyl}-4-piperidinyl)amino]methyl}-2,3-dihydro-1,4-benzodioxin-5-carbonitrile hydrochloride수율 42.3%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A suspension of (2R)-2-[(4-amino-1-piperidinyl)methyl]-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylene-3,8-dione (for a preparation see Example 16A(j)) (60 mg, 0.199 mmol) and 7-formyl-2,3-dihydro-1,4-benzodioxin-5-carbonitrile (for a synthesis see WO06014580 Preparation 13 or WO2007122258, Example 31(d)) (37.7 mg, 0.199 mmol) in chloroform (2 ml) and methanol (0.100 ml) at room temperature under nitrogen was treated with sodium triacetoxyborohydride (127 mg, 0.597 mmol) and stirred for 90 min. This was then treated with saturated aqueous NaHCO3(10 ml) and extracted with 20% methanol/DCM (3×25 ml). The combined organic extracts were dried (NaSO4), filtered, evaporated and purified using silica chromatography (0-20% methanol/DCM) to give the free base of the title compound as a yellow gum (40 mg, 42.3%).

후처리

  1. extractionextracted with 20% methanol/DCM (3×25 ml)
  2. dry with materialThe combined organic extracts were dried (NaSO4)
  3. filtrationfiltered
  4. customevaporated
  5. custompurified

출처 및 근거

ORD 기록
ord-1570d810b1ee476780e0b5594366d4ac
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389524B2

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