Benzaldehyde → Methyl 1-(4-(4-oxo-2-phenyl-4H-chromen-6-yl)benzyl)azetidine-3-carboxylate

HRID 717675Notes

Reaction equation

HRID 717675 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=3)[CH:10]=2)[O:5][C:4]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:3]1.[CH3:26][N:27]1CCC(=C2C3N=CC=CC=3CCC3C=CC=CC2=3)C[CH2:28]1.[CH:48](=O)C1C=CC=CC=1.Cl.N([CH2:59][C:60]([OH:62])=[O:61])C>>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[CH:19]=[CH:18][C:15]([CH2:16][N:27]4[CH2:28][CH:59]([C:60]([O:62][CH3:48])=[O:61])[CH2:26]4)=[CH:14][CH:13]=3)[CH:10]=2)[O:5][C:4]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:3]1

Participants

5

Reactant 4

HCID 240BenzaldehydeHCID 19861AzatadineHCID 69483Glycine, N-methyl-, hydrochloride (1:1)HCID 866606184-(4-Oxo-2-phenyl-4H-chromen-6-yl)benzaldehyde

Product 1

HCID 66615050Methyl 1-(4-(4-oxo-2-phenyl-4H-chromen-6-yl)benzyl)azetidine-3-carboxylateYield 31%

Procedure

When the product of Step C and azatadine 3 methylcarboxylate hydrochloride were substituted for -(5-(((4-fluorophenyl))isopropyl)amino)methyl)thiophen-2-yl)benzaldehyde and sarcosine hydrochloride, respectively, as in Example 22, Step C, the similar procedure afforded the title compound in 31% yield, as light green paste. 1H-NMR (CDCl3) 8.43 (d, 1H, J=2.29 Hz); 7.96-7.91 (m, 3H); 7.63 (d, 3H); 7.54-7.39 (m, 3H); 7.38 (d, 2H, J=8.18 Hz); 6.85 (s, 1H); 3.73 (s, 3H); 3.71 (s, 2H); 3.71-3.62 (broad, 2H); 3.42-3.35 (b, 3H).

Sources & evidence

ORD record
ord-a955f749d61d49db8af5d19afc346ce6
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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