2-(Thiophen-2-yl)benzoic acid → HCID 52918932, compound

HRID 1193146Notes

Reaction equation

HRID 1193146 reaction equation
[C@@H:1]12[N:8]([C:9]3[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([N:16]([CH3:18])[CH3:17])[N:10]=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>>[CH3:18][N:16]([CH3:17])[C:11]1[N:10]=[C:9]([N:8]2[C@@H:1]3[C@@H:6]([CH2:5][CH2:4][N:3]([C:41]([C:40]4[CH:44]=[C:36]([F:35])[CH:37]=[CH:38][C:39]=4[N:45]4[N:49]=[CH:48][CH:47]=[N:46]4)=[O:42])[CH2:2]3)[CH2:7]2)[CH:14]=[C:13]([CH3:15])[N:12]=1

Participants

5

Reactant 4

HCID 51056232-(Thiophen-2-yl)benzoic acidHCID 670869485-fluoro-2-(2H-1,2,3-triazol-2-yl)benzoic acid2×HCID 68156860HCID 68156860, compoundHCID 68156939(1R,6S)-8-(4,6-Dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane

Product 1

HCID 52918932HCID 52918932, compound

Procedure

The title compound was prepared in a manner analogous to Example 1, substituting (1R,6S)-[4-(3,8-diaza-bicyclo[4.2.0]oct-8-yl)-6-methyl-pyrimidin-2-yl]-dimethyl-amine (Intermediate 8) 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. MS (ESI) mass calcd. for C22H25FN8O, 436.49; m/z found 437.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.14-6.61 (m, 5H), 5.82-5.45 (m, 1H), 4.75-3.27 (m, 6H), 3.22-2.55 (m, 8H), 2.37-1.78 m (m, 5H).

Sources & evidence

ORD record
ord-c542d206eec8421f83f93f20ebcad4f7
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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