Formaldehyde → HCID 118022357, compound

HRID 575600Notes

Reaction equation

N[C:2]1[C:7](=[O:8])[N:6]([CH3:9])[CH:5]=[C:4]([C:10]2[CH:11]=[CH:12][C:13]([O:21][CH3:22])=[C:14]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:15]=2)[CH:3]=1.[CH2:23]=O.[BH3-][C:26]#[N:27].[Na+]>CO.CC(O)=O>[CH3:23][N:27]([CH3:26])[C:2]1[C:7](=[O:8])[N:6]([CH3:9])[CH:5]=[C:4]([C:10]2[CH:11]=[CH:12][C:13]([O:21][CH3:22])=[C:14]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:15]=2)[CH:3]=1

Participants

Conditions

Temperature: 30 °C

Procedure

To a solution of compound from Example 109 (64.6 mg, 0.2 mmol) in MeOH (3 mL) and AcOH (0.3 mL) was added HCHO (30.0 mg, 1.0 mmol) dropwise with stirring at 30° C. NaBH3CN (61 mg, 1.0 mol) was added in portions at 30° C. The reaction mixture was stirred for 2 h at 30° C. It was then quenched with saturated aqueous NH4Cl (5 mL), extracted with EtOAc (20 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel (PE:EA=2:3) to give the title compound (30 mg, 43%) as a light green solid. 1H NMR (Methanol-d4 400 MHz): δ 7.54 (d, J=2.4 Hz, 1H), 7.47 (d, J=2.4 Hz, 1H), 7.37 (dd, J1=2.4, J2=8.4 Hz, 1H), 7.11 (d, J=8.4 Hz, 1H), 7.04 (d, J=2.4 Hz, 1H), 3.93 (s, 3H), 3.63 (s, 3H), 2.94 (s, 3H), 2.86 (s, 6H). LCMS (M+H)+ 352.

Workup

stirringThe reaction mixture was stirred for 2 h at 30° C
customIt was then quenched with saturated aqueous NH4Cl (5 mL)
extractionextracted with EtOAc (20 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by column chromatography on silica gel (PE:EA=2:3)

Sources & evidence

ORD record: ord-40e6eb80c0a54c8badb5552dc80327ea
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034900B2

Reaction notes

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