Ammonium Acetate → (3R)-1-[7-(1-aminoethyl)-5-chloroquinolin-8-yl]pyrrolidin-3-ol

HRID 1192499노트

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HRID 1192499 반응식
[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=O)[CH3:13])[C:9]([N:15]2[CH2:19][CH2:18][C@@H:17]([OH:20])[CH2:16]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C([O-])(=O)C.[NH4+].C([BH3-])#[N:27].[Na+]>CO.C(#N)C>[NH2:27][CH:12]([C:10]1[C:9]([N:15]2[CH2:19][CH2:18][C@@H:17]([OH:20])[CH2:16]2)=[C:8]2[C:3]([CH:4]=[CH:5][CH:6]=[N:7]2)=[C:2]([Cl:1])[CH:11]=1)[CH3:13]

참가 물질

6

반응물 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 673019081-{5-chloro-8-[(3R)-3-hydroxypyrrolidin-1-yl]quinolin-7-yl}ethanone

생성물 1

HCID 67246897(3R)-1-[7-(1-aminoethyl)-5-chloroquinolin-8-yl]pyrrolidin-3-ol

시약·촉매·용매 2

HCID 887Methanol용매HCID 6342Acetonitrile용매

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온도
65 °C

실험 절차

A mixture of 1-{5-chloro-8-[(3R)-3-hydroxypyrrolidin-1-yl]quinolin-7-yl}ethanone (95 mg, 0.33 mmol) and ammonium acetate (252 mg, 3.27 mmol) in methanol (1.8 mL) and acetonitrile (1.9 mL) was heated at 65° C. in a sealed tube for 30 minutes. After cooling, sodium cyanoborohydride (41.1 mg, 0.653 mmol) was added to the resultant mixture. The reaction was heated at 65° C. for another 4 hours, then cooled to room temperature and quenched with saturated sodium bicarbonate. The mixture was then extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and evaporated to dryness (58 mg, 60%). The residue was used directly in the next step. LCMS calculated for C15H19ClN3O(M+H)+: m/z=292.1; found: 292.1.

후처리

  1. temperatureAfter cooling
  2. temperatureThe reaction was heated at 65° C. for another 4 hours
  3. temperaturecooled to room temperature
  4. customquenched with saturated sodium bicarbonate
  5. extractionThe mixture was then extracted with dichloromethane
  6. dry with materialThe combined extracts were dried over magnesium sulfate
  7. customevaporated to dryness (58 mg, 60%)

출처 및 근거

ORD 기록
ord-67f35ca2da4b4dae9a8e754e8528c486
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680108B2

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