Benzaldehyde → Methyl-1-(4-(12-oxo-12H-chromeno[2,3-b]quinolin-2-yl)benzyl)azetidine-3-carboxylate

HRID 717684Notes

Reaction equation

[O:1]=[C:2]1[C:19]2[C:10](=[N:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[CH:18]=2)[O:9][C:8]2[C:3]1=[CH:4][C:5]([C:20]1[CH:27]=[CH:26][C:23](C=O)=[CH:22][CH:21]=1)=[CH:6][CH:7]=2.CN1CCC(=C2[C:43]3[N:44]=[CH:45]C=[CH:47][C:42]=3[CH2:41]CC3C=CC=CC2=3)CC1.[CH:50](=[O:57])C1C=CC=CC=1.Cl.N(CC(O)=[O:63])C>>[CH3:50][O:57][C:41]([CH:42]1[CH2:47][N:44]([CH2:45][C:23]2[CH:22]=[CH:21][C:20]([C:5]3[CH:4]=[C:3]4[C:8](=[CH:7][CH:6]=3)[O:9][C:10]3=[N:11][C:12]5[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=5[CH:18]=[C:19]3[C:2]4=[O:1])=[CH:27][CH:26]=2)[CH2:43]1)=[O:63]

Participants

Reactant 4

HCID 240Benzaldehyde

HCID 19861Azatadine

HCID 69483Glycine, N-methyl-, hydrochloride (1:1)

HCID 866606214-(12-Oxo-12H-chromeno[2,3-b]quinolin-2-yl)benzaldehyde

Product 1

HCID 66615027Methyl-1-(4-(12-oxo-12H-chromeno[2,3-b]quinolin-2-yl)benzyl)azetidine-3-carboxylateYield 48%

Procedure

When the product of Step C and azatadine 3 methylcarboxylate hydrochloride were substituted for 4-(5-(((4-fluorophenyl))isopropyl)amino)methyl)thiophen-2-yl)benzaldehyde and sarcosine hydrochloride, respectively, in Example 22, Step C, the similar procedure afforded the title compound in 48% yield, as pale paste. 1H-NMR (CDCl3) 9.32 (s, 1H); 8.53 (s, 1H); 8.12-8.07 (m, 2H); 8.00 (dd, 1H, J=8.7, 2.4 Hz); 7.91 (t, 1H, J=5.55 Hz); 7.7-7.6 (m, 4H); 7.38 (d, 2H, J=8.22 Hz); 3.71 (s, 3H); 3.67 (s, 2H); 3.57-3.53 (m, 2H); 3.39-3.35 (m, 3H).

Sources & evidence

ORD record: ord-dca1efb0db714f68a91e4e7116bab56d
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193716B2

Reaction notes

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