Methyl-1-(4-((5-chlorobenzofuran-3-yl)methoxy)benzyl)azetidine-3-carboxylate → 1-(4-(12-oxo-12H-chromeno[2,3-b]quinolin-2-yl)benzyl)azetidine-3-carboxylic acid

HRID 717685Notes

Reaction equation

HRID 717685 reaction equation
C[O:2][C:3]([CH:5]1[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:17]=[C:18]4[C:31](=[CH:32][CH:33]=3)[O:30][C:21]3=[N:22][C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=5[CH:29]=[C:20]3[C:19]4=[O:34])=[CH:12][CH:11]=2)[CH2:6]1)=[O:4].COC(C1CN(CC2C=CC(OCC3C4C=C(Cl)C=CC=4OC=3)=CC=2)C1)=O>>[O:34]=[C:19]1[C:20]2[C:21](=[N:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=3[CH:29]=2)[O:30][C:31]2[C:18]1=[CH:17][C:16]([C:13]1[CH:14]=[CH:15][C:10]([CH2:9][N:7]3[CH2:8][CH:5]([C:3]([OH:4])=[O:2])[CH2:6]3)=[CH:11][CH:12]=1)=[CH:33][CH:32]=2

Participants

3

Reactant 2

HCID 66614996Methyl-1-(4-((5-chlorobenzofuran-3-yl)methoxy)benzyl)azetidine-3-carboxylateHCID 66615027Methyl-1-(4-(12-oxo-12H-chromeno[2,3-b]quinolin-2-yl)benzyl)azetidine-3-carboxylate

Product 1

HCID 461998301-(4-(12-oxo-12H-chromeno[2,3-b]quinolin-2-yl)benzyl)azetidine-3-carboxylic acidYield 50%

Procedure

When the product of Step D was substituted for methyl-1-(4-((5-chlorobenzofuran-3-yl)methoxy)benzyl)azetidine-3-carboxylate in Example 25, Step E, the similar procedure afforded the title compound in 50% yield, as yellow solid. 1H-NMR (CDCl+CD3OD) 9.25 (broad s, 1H); 8.44 (m, 2H); 7.76-7.54 (m, 5H); 4.31-4.07 (m, 4H); 4.27-3.95 (m, 2H).

Sources & evidence

ORD record
ord-b78dcb7d1166475f81da269d2b319de6
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

Loading…