Benzaldehyde → Methyl-1-((4'-(3-(3-(trifluoromethyl)phenyl)but-2-enoyl)biphenyl-4-yl)methyl)azetidine-3-carboxylate

HRID 717672Notes

Reaction equation

[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([C:9]([CH3:27])=[CH:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22](C=O)=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)=[O:12])[CH:6]=[CH:7][CH:8]=1.CN1CCC(=C2[C:45]3[N:46]=[CH:47]C=[CH:49][C:44]=3[CH2:43]CC3C=CC=CC2=3)CC1.[CH:52](=[O:59])C1C=CC=CC=1.Cl.N(CC(O)=[O:65])C>>[CH3:52][O:59][C:43]([CH:44]1[CH2:49][N:46]([CH2:47][C:22]2[CH:23]=[CH:24][C:19]([C:16]3[CH:17]=[CH:18][C:13]([C:11](=[O:12])[CH:10]=[C:9]([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:29])[F:28])[CH:4]=4)[CH3:27])=[CH:14][CH:15]=3)=[CH:20][CH:21]=2)[CH2:45]1)=[O:65]

Participants

Reactant 4

HCID 240Benzaldehyde

HCID 19861Azatadine

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

HCID 866606174'-(3-(3-(Trifluoromethyl)phenyl)but-2-enoyl)biphenyl-4-carbaldehyde

Product 1

HCID 68002037Methyl-1-((4'-(3-(3-(trifluoromethyl)phenyl)but-2-enoyl)biphenyl-4-yl)methyl)azetidine-3-carboxylateYield 58%

Procedure

When the product of Step D 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 58% yield, as a pale paste. 1H-NMR (CDCl3) 8.04 (d, 2H, J=8.4 Hz); 7.78-7.51 (m, 8H); 7.4 (d, 2H, J=8.2 Hz); 7.16 (d, 1H, J=1.21 Hz); 3.76 (s, 2H); 3.7 (s, 3H); 3.73-3.62 (m, 4H); 3.47-3.41 (m, 3H); 2.58 (bs, 3H).

Sources & evidence

ORD record: ord-523c7719b479487798e1766839d21466
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193716B2

Reaction notes

Loading…