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Ammonium Acetate → 1-{5-chloro-8-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]quinolin-7-yl]ethanamine

HRID 1192505
Notes
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Reaction equation

HRID 1192505 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=O)[CH3:13])[C:9]([N:15]2[CH2:19][CH2:18][CH2:17][C@@H:16]2[CH2:20][O:21][CH3:22])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C([O-])(=O)C.[NH4+].C([BH3-])#[N:29].[Na+]>CO.C(#N)C>[Cl:1][C:2]1[CH:11]=[C:10]([CH:12]([NH2:29])[CH3:13])[C:9]([N:15]2[CH2:19][CH2:18][CH2:17][C@@H:16]2[CH2:20][O:21][CH3:22])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 673016501-{5-chloro-8-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]quinolin-7-yl}ethanone

Product 1

HCID 673009761-{5-chloro-8-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]quinolin-7-yl]ethanamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1-{5-chloro-8-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]quinolin-7-yl}ethanone (14 mg, 0.044 mmol) and ammonium acetate (33.8 mg, 0.439 mmol) in methanol (0.25 mL,) and acetonitrile (0.25 mL) was heated at 65° C. in a sealed tube for 30 minutes. After cooling, sodium cyanoborohydride (5.52 mg, 0.0878 mmol) was added to the resultant mixture. The reaction was heated at 65° C. for another 4 hours, then cooled to room temperature, quenched with saturated sodium bicarbonate, and extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and evaporated to dryness. The residue was used directly in the next step. LCMS calculated for C17H23ClN3O(M+H)+: m/z=320.2; found: 302.1.

Workup

  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. extractionextracted with dichloromethane
  6. dry with materialThe combined extracts were dried over magnesium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-914418fe539644998c2fc5e55ff4bd5f
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08680108B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes