2-(Thiophen-2-yl)benzoic acid → HCID 52920164, compound

HRID 1193178Notes

Reaction equation

HRID 1193178 reaction equation
C[C:2]1[N:3]=[CH:4][C:5]([N:9]2[C@@H:16]3[C@@H:11]([CH2:12][CH2:13][NH:14][CH2:15]3)[CH2:10]2)=[N:6][C:7]=1C.[CH3:17]C1C=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>[CH3:17][C:4]1[C:5]([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:6][CH:7]=[CH:2][N:3]=1

Participants

6

Reactant 4

HCID 51056232-(Thiophen-2-yl)benzoic acidHCID 213135922-(2H-1,2,3-Triazol-2-yl)benzoic acid2×HCID 67116879HCID 67116879, compoundHCID 68156939(1R,6S)-8-(4,6-Dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane

Product 1

HCID 52920164HCID 52920164, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in a manner analogous to Example 1, substituting (1R,6S)-8-(3-methylpyrazin-2-yl)-3,8-diazabicyclo[4.2.0]octane (Intermediate 31) 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 376.1 [M+H]+. 1H NMR (CD3OD): 8.08-8.01 (m, 1H), 7.98-7.88 (m, 2H), 7.84-7.78 (m, 1H), 7.70-7.38 (m, 4H), 4.55-3.84 (m, 4H), 3.75-3.11 (m, 3H), 2.70-2.29 (m, 4H), 2.22-1.48 (m, 2H).

Sources & evidence

ORD record
ord-fb5d28c9fe1140baa7b7e9d8e4696ce3
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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