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

HRID 1193172Notes

Reaction equation

HRID 1193172 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.[N:33]1[N:34]([C:38]2[CH:46]=[CH:45][CH:44]=[CH:43][C:39]=2[C:40](O)=[O:41])[N:35]=[CH:36][CH:37]=1.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:40]([C:39]4[CH:43]=[CH:44][CH:45]=[CH:46][C:38]=4[N:34]4[N:35]=[CH:36][CH:37]=[N:33]4)=[O:41])[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 213135922-(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 52919940(1R,6S)-8-(3,6-Dimethylpyrazin-2-yl)-3-{[2-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}-3,8-diazabicyclo[4.2.0]octane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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 2-[1,2,3]triazol-2-yl-benzoic acid (Intermediate 14) for 2-thiophen-2-yl-benzoic acid and DCM in place of DMF. DCM was used in place of DMF. MS (ESI) mass calcd. For O21H23N7O, 389.46; m/z found 390.1 [M+H]+. 1H NMR (CDCl3): 8.03-7.91 (m, 1H), 7.81-7.64 (m, 2H), 7.54-7.20 (m, 3H), 6.99-6.87 (m, 1H), 4.87-3.93 (m, 4H), 3.78-3.48 (m, 2H), 3.29-2.75 (m, 2H), 2.39-2.29 (m, 4H), 2.06-2.02 (m, 4H).

Sources & evidence

ORD record
ord-332de79adab543699b1e75986f25dea5
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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