Formaldehyde → HCID 57742045, compound

HRID 2171963Notes

Reaction equation

[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O.[O:17]=[C:18]1[C:27]2([CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH2:26][C:25]2[C:20](=[N:21][CH:22]=[C:23](/[CH:33]=[CH:34]/[C:35]([OH:37])=[O:36])[CH:24]=2)[NH:19]1>ClCCCl>[CH3:1][N:30]1[CH2:31][CH2:32][C:27]2([CH2:26][C:25]3[C:20](=[N:21][CH:22]=[C:23](/[CH:33]=[CH:34]/[C:35]([OH:37])=[O:36])[CH:24]=3)[NH:19][C:18]2=[O:17])[CH2:28][CH2:29]1

Participants

Conditions

Temperature: 70 °C

Procedure

Sodium triacetoxyborohydride (671 mg, 3.17 mmol) and paraformaldehyde (95 mg, 3.17 mmol) were successively added to a suspension of (E)-3-(2-oxo-2,4-dihydro-1H-spiro[[1,8]naphthyridine-3,4′-piperidine]-6-yl)acrylic acid (455 mg, 1.58 mmol) in 1,2-dichloroethane (40 mL) at room temperature. The reaction mixture was then heated to 70° C. and stirred for 2 hours. The reaction mixture was cooled to room temperature, the precipitated product filtered and washed with H2O (50 mL) and MeOH (3×50 mL) and dried. The title product was obtained as a white solid (319 mg, 66%, py 74.1%).

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationthe precipitated product filtered
washwashed with H2O (50 mL) and MeOH (3×50 mL)
customdried

Sources & evidence

ORD record: ord-5cbff1bba7fd40e69a3f30f6638aa5d9
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051321B2

Reaction notes

Loading…