Benzaldehyde → Methyl-1-(4-(4-oxo-4-(3,4,5-trimethoxyphenyl)but-2-en-2-yl)benzyl)azetidine-3-carboxylate

HRID 717668Notes

Reaction equation

[O:1]=[C:2]([C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=1)[CH:3]=[C:4]([C:6]1[CH:13]=[CH:12][C:9](C=O)=[CH:8][CH:7]=1)[CH3:5].CN1CCC(=C2[C:41]3[N:42]=[CH:43]C=[CH:45][C:40]=3[CH2:39]CC3C=CC=CC2=3)CC1.[CH:48](=[O:55])C1C=CC=CC=1.Cl.N(CC(O)=[O:61])C>>[CH3:48][O:55][C:39]([CH:40]1[CH2:45][N:42]([CH2:43][C:9]2[CH:12]=[CH:13][C:6]([C:4](=[CH:3][C:2](=[O:1])[C:14]3[CH:15]=[C:16]([O:24][CH3:25])[C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=3)[CH3:5])=[CH:7][CH:8]=2)[CH2:41]1)=[O:61]

Participants

Reactant 4

HCID 240Benzaldehyde

HCID 19861Azatadine

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

HCID 866606154-(4-Oxo-4-(3,4,5-trimethoxyphenyl)but-2-en-2-yl)benzaldehyde

Product 1

HCID 66615083Methyl-1-(4-(4-oxo-4-(3,4,5-trimethoxyphenyl)but-2-en-2-yl)benzyl)azetidine-3-carboxylateYield 66%

Procedure

When the product of Step B 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 process afforded the title compound in 66% yield, as pale paste. 1H-NMR (CDCl3) 7.49 (d, 2H, J=8.28 Hz); 7.30 (d, 2H, J=8.29 Hz); 7.22 (s, 2H), 7.06 (s, 1H); 3.90 (s, 9H); 3.68 (s, 3H); 3.64 (s, 2H); 3.56-3.52 (m, 2H); 3.37-3.32 (m, 3H).

Sources & evidence

ORD record: ord-e94cfb7787174613bd459b85772966f6
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193716B2

Reaction notes

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