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

HRID 1193174Notes

Reaction equation

HRID 1193174 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:42]=[CH:41][CH:40]=[C:39]([N:43]2[N:47]=[CH:46][CH:45]=[N:44]2)[C:35]=1[C:36](O)=[O:37].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:36]([C:35]4[C:39]([N:43]5[N:47]=[CH:46][CH:45]=[N:44]5)=[CH:40][CH:41]=[CH:42][C:34]=4[F:33])=[O:37])[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 670866272-Fluoro-6-(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 52920051(1R,6S)-8-(3,6-Dimethylpyrazin-2-yl)-3-{[2-fluoro-6-(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 2-Fluoro-6-[1,2,3]triazol-2-yl-benzoic acid (Intermediate 15) 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): 7.96-7.23 (m, 6H), 4.50-4.44 (m, 1H), 4.31-4.19 (m, 2H), 4.11-3.77 (m, 3H), 3.62-3.42 (m, 1H), 2.86-2.77 (m, 1H), 2.40-2.36 (m, 3H), 2.31-2.05 (m, 2H), 2.04-1.92 (m, 3H).

Sources & evidence

ORD record
ord-4ff3afbde88a4b63a7c1babf92cbbeea
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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