2-(Thiophen-2-yl)benzoic acid → HCID 67116500, compound

HRID 1193190Notes

Reaction equation

HRID 1193190 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[C:37]([N:45]2[N:49]=[CH:48][CH:47]=[N:46]2)=[C:38]([CH:42]=[CH:43][CH:44]=1)[C:39](O)=[O:40].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:39]([C:38]5[CH:42]=[CH:43][CH:44]=[C:36]([F:35])[C:37]=5[N:45]5[N:49]=[CH:48][CH:47]=[N:46]5)=[O:40])[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 670865493-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 67116500HCID 67116500, 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 3-fluoro-2-(2H-1,2,3-triazol-2-yl)benzoic acid (Intermediate 50) 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): 8.01-7.35 (m, 5H), 7.25-6.81 (m, 3H), 4.75-4.24 (m, 2H), 4.12-3.03 (m, 6H), 2.25-1.81 (m, 2H).

Sources & evidence

ORD record
ord-21ccac3f19ad4ade8f55d2ea272cb29c
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

Loading…