2-(Thiophen-2-yl)benzoic acid → HCID 67116977, compound

HRID 1193187Notes

Reaction equation

HRID 1193187 reaction equation
[C@@H:1]12[N:8]([C:9]3[O:10][C:11]4[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:12]=4[N:13]=3)[CH2:7][C@@H:6]1[CH2:5][CH2:4][NH:3][CH2:2]2.CC1C=C(C)N=C(N2[C@@H]3[C@@H](CCNC3)C2)N=1.[N:35]1[N:36]([C:40]2[CH:48]=[CH:47][CH:46]=[CH:45][C:41]=2[C:42](O)=[O:43])[N:37]=[CH:38][CH:39]=1.S1C=CC=C1C1C=CC=CC=1C(O)=O>C(Cl)Cl>[Cl:18][C:15]1[CH:16]=[CH:17][C:11]2[O:10][C:9]([N:8]3[C@@H:1]4[C@@H:6]([CH2:5][CH2:4][N:3]([C:42]([C:41]5[CH:45]=[CH:46][CH:47]=[CH:48][C:40]=5[N:36]5[N:37]=[CH:38][CH:39]=[N:35]5)=[O:43])[CH2:2]4)[CH2:7]3)=[N:13][C:12]=2[CH:14]=1

Participants

6

Reactant 4

HCID 51056232-(Thiophen-2-yl)benzoic acidHCID 213135922-(2H-1,2,3-Triazol-2-yl)benzoic acid2×HCID 671167812-((1R,6S)-3,8-Diazabicyclo[4.2.0]octan-8-yl)-5-chlorobenzo[d]oxazoleHCID 68156939(1R,6S)-8-(4,6-Dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane

Product 1

HCID 67116977HCID 67116977, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in a manner analogous to Example 1, substituting 2-((1R,6S)-3,8-diazabicyclo[4.2.0]octan-8-yl)-5-chlorobenzo[d]oxazole (Intermediate 32) 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 C22H19ClN6O2, 434.89; m/z found 435.1 [M+H]+. 1H NMR (CD3OD): 8.03-7.28 (m, 6H), 7.23-6.88 (m, 3H), 4.72-4.54 (m, 1H), 4.35-3.96 (m, 3H), 3.90-3.35 (m, 3H), 3.13-1.71 (m, 3H).

Sources & evidence

ORD record
ord-036eb463caad4f3280000b868be6146c
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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