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2-Amino-5-fluoropyridine → rac-cis-(2-(((5-Fluoropyridin-2-yl)amino)methyl)-3-methylpiperidin-1-yl)(5-(4-fluorophenyl)-2-methylthiazol-4-yl)methanone

HRID 60846
Notes
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Reaction equation

HRID 60846 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH3:13])=[N:10][C:9]=2[C:14]([N:16]2[CH2:21][CH2:20][CH2:19][C@H:18]([CH3:22])[C@@H:17]2[CH:23]=O)=[O:15])=[CH:4][CH:3]=1.[F:25][C:26]1[CH:27]=[CH:28][C:29]([NH2:32])=[N:30][CH:31]=1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C.CCOC(C)=O.C([O-])(O)=O.[Na+]>[F:25][C:26]1[CH:27]=[CH:28][C:29]([NH:32][CH2:23][C@H:17]2[C@@H:18]([CH3:22])[CH2:19][CH2:20][CH2:21][N:16]2[C:14]([C:9]2[N:10]=[C:11]([CH3:13])[S:12][C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[O:15])=[N:30][CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 27377012-Amino-5-fluoropyridineHCID 5003444Sodium cyanoborohydrideHCID 131737135rac-cis-1-(5-(4-Fluorophenyl)-2-methylthiazole-4-carbonyl)-3-methylpiperidine-2-carbaldehyde

Product 1

HCID 131737136rac-cis-(2-(((5-Fluoropyridin-2-yl)amino)methyl)-3-methylpiperidin-1-yl)(5-(4-fluorophenyl)-2-methylthiazol-4-yl)methanone

Reagents, catalysts & solvents 3

HCID 8857
Ethyl Acetate
Solvent
HCID 516892Sodium BicarbonateSolvent
HCID 10129899Acetic acid methanolSolvent

Procedure

To a stirred solution of rac-cis-1-(5-(4-fluorophenyl)-2-methylthiazole-4-carbonyl)-3-methylpiperidine-2-carbaldehyde and 5-fluoropyridin-2-amine in methanol/acetic acid (50:1) was added sodium cyanoborohydride at 0° C. The reaction was then stirred at rt overnight. After ˜16 h, the reaction mixture was transferred to a seperatory funnel, diluted with EtOAc, saturated NaHCO3 and the layers separated. The organic layer was washed with water, brine, dried (MgSO4), and concentrated in vacuo. The crude reaction mixture was purified by reverse-phase preparative HPLC to afford the title compound. MS (ESI) 443.2 (M+H).

Workup

  1. waitAfter ˜16 h
  2. customthe reaction mixture was transferred to a seperatory funnel
  3. customthe layers separated
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude reaction mixture
  8. customwas purified by reverse-phase preparative HPLC

Sources & evidence

ORD record
ord-dbdb52e682a049b0969c0e448bb73064
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09440982B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes