2-(Thiophen-2-yl)benzoic acid → HCID 52920053, compound

HRID 1193175Notes

Reaction equation

HRID 1193175 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]([N:8]2[C@@H:15]3[C@@H:10]([CH2:11][CH2:12][NH:13][CH2:14]3)[CH2:9]2)=[N:6][CH:7]=1.CC1C=C(C)N=C(N2[C@@H]3[C@@H](CCNC3)C2)N=1.[N:32]1[N:33]([C:37]2[CH:45]=[CH:44][CH:43]=[CH:42][C:38]=2[C:39](O)=[O:40])[N:34]=[CH:35][CH:36]=1.S1C=CC=C1C1C=CC=CC=1C(O)=O>C(Cl)Cl>[CH3:1][C:2]1[N:3]=[CH:4][C:5]([N:8]2[C@@H:15]3[C@@H:10]([CH2:11][CH2:12][N:13]([C:39]([C:38]4[CH:42]=[CH:43][CH:44]=[CH:45][C:37]=4[N:33]4[N:34]=[CH:35][CH:36]=[N:32]4)=[O:40])[CH2:14]3)[CH2:9]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 51056232-(Thiophen-2-yl)benzoic acidHCID 213135922-(2H-1,2,3-Triazol-2-yl)benzoic acid2×HCID 67116692(1R,6S)-8-(5-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 52920053HCID 52920053, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in a manner analogous to Example 1, substituting (1R,6S)-8-(5-methylpyrazin-2-yl)-3,8-diazabicyclo[4.2.0]octane (Intermediate 29) 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. DCM was used in place of DMF. MS (ESI) mass calcd. For C20H21N7O, 375.44; m/z found 376.0 [M+H]+. 1H NMR (CDCl3): 8.06-7.78 (m, 3H), 7.72-7.44 (m, 3H), 7.39-7.28 (m, 1H), 7.16-6.96 (m, 1H), 4.56-3.98 (m, 4H), 3.80-2.96 (m, 4H), 2.46-2.03 (m, 5H).

Sources & evidence

ORD record
ord-91ee8c539e984e9aabf7a7ed9176299e
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

Loading…