2-(Thiophen-2-yl)benzoic acid → HCID 52920285, compound

HRID 1193181Notes

Reaction equation

HRID 1193181 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[C@@H:15]3[C@@H:10]([CH2:11][CH2:12][NH:13][CH2:14]3)[CH2:9]2)[CH:5]=[N:4][CH:3]=1.CC1C=C(C)N=C(N2[C@@H]3[C@@H](CCNC3)C2)N=1.[F:32][C:33]1[CH:34]=[CH:35][C:36]([N:42]2[N:46]=[CH:45][CH:44]=[N:43]2)=[C:37]([CH:41]=1)[C:38](O)=[O:39].S1C=CC=C1C1C=CC=CC=1C(O)=O>C(Cl)Cl>[F:32][C:33]1[CH:34]=[CH:35][C:36]([N:42]2[N:46]=[CH:45][CH:44]=[N:43]2)=[C:37]([C:38]([N:13]2[CH2:12][CH2:11][C@@H:10]3[C@@H:15]([N:8]([C:6]4[CH:5]=[N:4][CH:3]=[C:2]([CH3:1])[N:7]=4)[CH2:9]3)[CH2:14]2)=[O:39])[CH:41]=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 67116766(1R,6S)-8-(6-Methylpyrazin-2-yl)-3,8-diazabicyclo[4.2.0]octaneHCID 68156939(1R,6S)-8-(4,6-Dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane

Product 1

HCID 52920285HCID 52920285, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in a manner analogous to Example 1, substituting (1R,6S)-8-(6-methylpyrazin-2-yl)-3,8-diazabicyclo[4.2.0]octane (Intermediate 30) 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 C20H20FN7O, 393.43; m/z found 394.1 [M+H]+. 1H NMR (CD3OD): 8.11-7.84 (m, 2H), 7.81-7.58 (m, 1H), 7.52-6.40 (m, 4H), 4.70-4.26 (m, 1H), 4.23-3.67 (m, 4H), 3.67-3.40 (m, 1H), 3.12-1.53 (m, 7H).

Sources & evidence

ORD record
ord-28f1efdcbdf64eb78f5e692b45bfae22
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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