2-(Thiophen-2-yl)benzoic acid → (1R,6S)-8-(3,6-Dimethylpyrazin-2-yl)-3-{[5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}-3,8-diazabicyclo[4.2.0]octane

HRID 1193173Notes

Reaction equation

HRID 1193173 reaction equation
[CH3:1][C:2]1[C:3]([N:9]2[C@@H:16]3[C@@H:11]([CH2:12][CH2:13][NH:14][CH2:15]3)[CH2:10]2)=[N:4][C:5]([CH3:8])=[CH:6][N:7]=1.CC1C=C(C)N=C(N2[C@@H]3[C@@H](CCNC3)C2)N=1.[F:33][C:34]1[CH:35]=[CH:36][C:37]([N:43]2[N:47]=[CH:46][CH:45]=[N:44]2)=[C:38]([CH:42]=1)[C:39](O)=[O:40].S1C=CC=C1C1C=CC=CC=1C(O)=O>C(Cl)Cl>[CH3:1][C:2]1[C:3]([N:9]2[C@@H:16]3[C@@H:11]([CH2:12][CH2:13][N:14]([C:39]([C:38]4[CH:42]=[C:34]([F:33])[CH:35]=[CH:36][C:37]=4[N:43]4[N:47]=[CH:46][CH:45]=[N:44]4)=[O:40])[CH2:15]3)[CH2:10]2)=[N:4][C:5]([CH3:8])=[CH:6][N:7]=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 68156939(1R,6S)-8-(4,6-Dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octaneHCID 68157557(1R,6S)-8-(3,6-Dimethyl-pyrazin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane

Product 1

HCID 52920050(1R,6S)-8-(3,6-Dimethylpyrazin-2-yl)-3-{[5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}-3,8-diazabicyclo[4.2.0]octane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in a manner analogous to Example 1, substituting (1R,6S)-8-(3,6-Dimethyl-pyrazin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane (Intermediate 10) 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 C21H22FN7O, 407.45; m/z found 408.2 [M+H]+. 1H NMR (CD3OD): 8.05-7.84 (m, 2H), 7.66-7.24 (m, 4H), 4.59-3.44 (m, 7H), 3.04-2.31 (m, 6H), 2.09-2.96 (m, 3H).

Sources & evidence

ORD record
ord-399d4c22bfa24cc8afed541d3e76b649
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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