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Formaldehyde → Narmafotinib

HRID 2272410
Notes
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Reaction equation

HRID 2272410 reaction equation
C=O.[CH3:3][O:4][C:5]1[CH:10]=[C:9]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:8]=[CH:7][C:6]=1[NH:17][C:18]1[N:23]=[C:22]([CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:32][C:33]([NH2:35])=[O:34])[C:21]([C:36]([F:39])([F:38])[F:37])=[CH:20][N:19]=1.[C:40](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CO.C(Cl)Cl>CO.C(OCC)(=O)C>[CH3:3][O:4][C:5]1[CH:10]=[C:9]([CH:11]2[CH2:16][CH2:15][N:14]([CH3:40])[CH2:13][CH2:12]2)[CH:8]=[CH:7][C:6]=1[NH:17][C:18]1[N:23]=[C:22]([CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:32][C:33]([NH2:35])=[O:34])[C:21]([C:36]([F:37])([F:38])[F:39])=[CH:20][N:19]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 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 60162119NarmafotinibYield 61%

Reagents, catalysts & solvents

2
HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Formaldehyde solution (37% aq.; 32 μL, 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 (3) (25 mg, 61%) as a solid; 1H NMR (400 MHz, CD2Cl2) δ 8.53 (s, 1H), 8.34 (d, J=8.3 Hz, 1H), 7.94 (s, 1H), 7.29-7.15 (m, 4H), 6.92 (dd, J=8.3, 1.4 Hz, 1H), 6.82 (d, J=1.7 Hz, 1H), 6.12 (bs, 1H), 5.84 (bs, 1H), 3.91 (s, 3H), 3.68 (s, 2H), 3.60 (d, J=10.6 Hz, 2H), 3.24-3.03 (m, 4H), 2.80 (s, 3H), 2.79 (m, 2H), 2.71 (m, 1H), 2.42-2.20 (m, 2H), 2.01 (m, 2H). LCMS Method C: rt 4.92 min; m/z 528.1 [M+1]+, 526.1 [M−1]−.

Sources & evidence

ORD record
ord-5fa1783c1d3d4870b8f2c2e4228e52b8
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09120761B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes