2-Naphthalenecarboxaldehyde → HCID 59581353, compound

HRID 386612Notes

Reaction equation

[NH2:1][CH2:2][C:3]([NH:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH2:11][C@@:10]1([C:18](=[O:19])[NH:17][C:16](=[O:20])[N:15]1[CH3:21])[CH2:9]2)=[O:4].[CH:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][C:23]=1[CH:32]=O.[BH4-].[Na+]>CO>[CH3:21][N:15]1[C@@:10]2([CH2:9][C:8]3[C:12](=[CH:13][CH:14]=[C:6]([NH:5][C:3](=[O:4])[CH2:2][NH:1][CH2:32][C:23]4[CH:24]=[CH:25][C:26]5[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=5)[CH:22]=4)[CH:7]=3)[CH2:11]2)[C:18](=[O:19])[NH:17][C:16]1=[O:20]

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred solution of 2-amino-N-[(4S)-3-methyl-2,5-dioxo-1′,3′-dihydrospiro[imidazolidine-4,2′-inden]-5′-yl]acetamide from Step B (80.0 mg, 0.277 mmol) and 2-naphthaldehyde (65.0 mg, 0.416 mmol), in MeOH (3 mL) was heated to 50° C. After 5 hours, no additional formation of the intermediate imine could be observed, so the reaction was cooled to 0° C., prior to the introduction of sodium borohydride (21.0 mg, 0.555 mmol). After 10 minutes the reaction was complete. The bulk of the solvent was remove in vacuo, and the resulting residue was applied to a silica gel column for purification, eluting with DCM:MeOH (10% conc. NH4OH)—98:2 to 92:8. Product containing fractions were pooled and concentrated in vacuo to give the title compound. MS: m/z=429 (M+1).

Workup

waitAfter 10 minutes the reaction was complete
customThe bulk of the solvent was remove in vacuo
customthe resulting residue was applied to a silica gel column for purification
washeluting with DCM
additionProduct containing fractions
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d8dd2045ec68499f8c578e7f59466d76
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372859B2

Reaction notes

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