2-(Thiophen-2-yl)benzoic acid → HCID 67117301, compound

HRID 1193189Notes

Reaction equation

HRID 1193189 reaction equation
[C@@H:1]12[N:8]([C:9]3[O:10][C:11]4[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:12]=4[N:13]=3)[CH2:7][C@@H:6]1[CH2:5][CH2:4][NH:3][CH2:2]2.CC1C=C(C)N=C(N2[C@@H]3[C@@H](CCNC3)C2)N=1.[F:35][C:36]1[CH:37]=[CH:38][C:39]([N:45]2[N:49]=[CH:48][CH:47]=[N:46]2)=[C:40]([CH:44]=1)[C:41](O)=[O:42].S1C=CC=C1C1C=CC=CC=1C(O)=O>C(Cl)Cl>[Cl:18][C:15]1[CH:16]=[CH:17][C:11]2[O:10][C:9]([N:8]3[C@@H:1]4[C@@H:6]([CH2:5][CH2:4][N:3]([C:41]([C:40]5[CH:44]=[C:36]([F:35])[CH:37]=[CH:38][C:39]=5[N:45]5[N:49]=[CH:48][CH:47]=[N:46]5)=[O:42])[CH2:2]4)[CH2:7]3)=[N:13][C:12]=2[CH:14]=1

Participants

6

Reactant 4

HCID 51056232-(Thiophen-2-yl)benzoic acidHCID 670869485-fluoro-2-(2H-1,2,3-triazol-2-yl)benzoic acid2×HCID 671167812-((1R,6S)-3,8-Diazabicyclo[4.2.0]octan-8-yl)-5-chlorobenzo[d]oxazoleHCID 68156939(1R,6S)-8-(4,6-Dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane

Product 1

HCID 67117301HCID 67117301, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in a manner analogous to Example 1, substituting 2-((1R,6S)-3,8-diazabicyclo[4.2.0]octan-8-yl)-5-chlorobenzo[d]oxazole (Intermediate 32) for (1R,6S)8-(4,6-dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane and 5-fluoro-2-[1,2,3]triazol-2-yl-benzoic acid (Intermediate 13) for 2-thiophen-2-yl-benzoic acid. DCM was used in place of DMF. MS (ESI) mass calcd. For C22H18ClFN6O2, 452.88; m/z found 453.1 [M+H]+. 1H NMR (CD3OD): 8.02-7.63 (m, 2H), 7.48-7.24 (m, 3H), 7.21-6.69 (m, 3H), 4.86-3.35 (m, 7H), 3.15-2.95 (m, 1H), 2.27-1.72 (m, 2H).

Sources & evidence

ORD record
ord-9baa2e72350646c1bb8fc528953d1928
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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