Formaldehyde → HCID 68283001, compound

HRID 1473155Notes

Reaction equation

HRID 1473155 reaction equation
C=O.[NH:3]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[N:21]=[C:20]([CH2:22][CH2:23][C:24]4[CH:25]=[C:26]([CH:30]=[CH:31][N:32]=4)[C:27]([NH2:29])=[O:28])[C:19]([C:33]([F:36])([F:35])[F:34])=[CH:18][N:17]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.[C:37](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(OCC)(=O)C>CO.CO.C(Cl)Cl>[CH3:37][N:3]1[CH2:4][CH2:5][CH:6]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[N:21]=[C:20]([CH2:22][CH2:23][C:24]4[CH:25]=[C:26]([CH:30]=[CH:31][N:32]=4)[C:27]([NH2:29])=[O:28])[C:19]([C:33]([F:36])([F:34])[F:35])=[CH:18][N:17]=3)=[CH:11][CH:10]=2)[CH2:7][CH2:8]1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 8857Ethyl AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 68282623HCID 68282623, compound

Product 1

HCID 68283001HCID 68283001, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Formaldehyde solution (37% aq; 24 μL, 0.30 mmol) was added to a solution of 2-(2-(2-((4-(Piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)isonicotinamide (I131) (28 mg, 60 μmol) in dry MeOH (2 mL). Sodium triacetoxyborohydride (63 mg, 0.30 mmol) was added and the resulting mixture stirred at room temperature for 2 hours under nitrogen. Ethyl acetate was added and the resulting solution adsorbed onto silica gel. Chromatography (SiO2, 0-50% MeOH/DCM) gave the title compound (34) (14 mg, 49%) as a colouless solid; 1H NMR (400 MHz, d4-MeOD) δ 8.58 (d, J=4.9 Hz, 1H), 8.51 (s, 1H), 7.73 (s, 1H), 7.61 (dd, J=5.2, 1.6 Hz, 1H), 7.53 (d, J=8.5 Hz, 2H), 7.18 (d, J=8.6 Hz, 2H), 3.51-3.31 (m, 4H), 2.99 (d, J=11.7 Hz, 2H), 2.56-2.44 (m, 1H), 2.32 (s, 3H), 2.15 (d, J=2.8 Hz, 2H), 1.87-1.70 (m, 4H). LCMS Method C: it 4.50 min; m/z 485.1 [M+1]+, 483.1 [M−1]−.

Sources & evidence

ORD record
ord-9bd3940a621643cca9265dad7e76e9a0
Source dataset
uspto-grants-2015_04
Patent number
US09012461B2

Reaction notes

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