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Acetaldehyde → 2-(2-(2-(2-((4-(1-Ethylpiperidin-4-yl)-2-methoxyphenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetamide

HRID 705749
Notes
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Reaction equation

HRID 705749 reaction equation
[CH:1](=O)[CH3:2].[CH3:4][O:5][C:6]1[CH:11]=[C:10]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:9]=[CH:8][C:7]=1[NH:18][C:19]1[N:24]=[C:23]([CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH2:33][C:34]([NH2:36])=[O:35])[C:22]([C:37]([F:40])([F:39])[F:38])=[CH:21][N:20]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CO.C(Cl)Cl>CO.C(OCC)(=O)C>[CH2:1]([N:15]1[CH2:16][CH2:17][CH:12]([C:10]2[CH:9]=[CH:8][C:7]([NH:18][C:19]3[N:24]=[C:23]([CH2:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[CH2:33][C:34]([NH2:36])=[O:35])[C:22]([C:37]([F:38])([F:39])[F:40])=[CH:21][N:20]=3)=[C:6]([O:5][CH3:4])[CH:11]=2)[CH2:13][CH2:14]1)[CH3:2]
ParticipantsProcedureSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 21226129Dichloromethane methanolHCID 601619862-(2-(2-(2-((2-Methoxy-4-(piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetamide

Product 1

HCID 601621202-(2-(2-(2-((4-(1-Ethylpiperidin-4-yl)-2-methoxyphenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetamide
Yield 24%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acetaldehyde (18 mg, 0.39 mmol) was added to a stirred solution of 2-(2-(2-(2-((2-methoxy-4-(piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetamide (2) (40 mg, 78 μmol) in dry MeOH (2 mL). Sodium triacetoxyborohydride (83 mg, 0.39 mmol) was added under nitrogen and the resulting mixture was stirred at room temperature for 2 hours. The crude mixture was diluted with ethyl acetate and adsorbed onto silica gel. Chromatography (SiO2, 0-20% MeOH/DCM) gave the title compound (4) (10 mg, 24%) as a light coloured solid; 1H NMR (400 MHz, CD2Cl2) δ 8.52 (s, 1H), 8.34 (d, J=8.3 Hz, 1H), 7.92 (s, 7.28-7.14 (m, 4H), 6.92 (d, J=8.3 Hz, 1H), 6.82 (d, J=1.7 Hz, 1H), 5.91 (bs, 1H), 5.87 (bs, 1H), 3.91 (s, 3H), 3.66 (s, 2H), 3.63 (m, 2H), 3.20-3.01 (m, 6H), 2.73 (d, J=11.7 Hz, 2H), 2.42-2.21 (m, 3H), 2.02 (d, J=18.0 Hz, 4H), 1.37 (t, J=7.3 Hz, 3H). LCMS Method C: rt 4.96 min; m/z 542.2 [M+1]+, 540.1 [M−1]−.

Sources & evidence

ORD record
ord-860e5ba3134f480fbfb3334005ec6034
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09174946B2

Reaction notes

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