6-methyl-3-(2H-1,2,3-triazol-2-yl)picolinic acid → HCID 90413409, compound

HRID 2175959Notes

Reaction equation

HRID 2175959 reaction equation
FC1C=CC(C2N=CC=CN=2)=C(C=1)C(O)=O.[CH3:17][C:18]1[N:23]=[C:22]([C:24]([OH:26])=O)[C:21]([N:27]2[N:31]=[CH:30][CH:29]=[N:28]2)=[CH:20][CH:19]=1.C(OC(N1[C@@H]2CC[C@H]1[C@H](COC1C=CC=CN=1)C2)=O)(C)(C)C.[Br:54][C:55]1[CH:56]=[CH:57][C:58]([O:61][CH2:62][CH:63]2[CH2:68][CH:67]3[NH:69][CH:64]2[CH2:65][CH2:66]3)=[N:59][CH:60]=1>>[Br:54][C:55]1[CH:56]=[CH:57][C:58]([O:61][CH2:62][CH:63]2[CH2:68][CH:67]3[N:69]([C:24]([C:22]4[C:21]([N:27]5[N:31]=[CH:30][CH:29]=[N:28]5)=[CH:20][CH:19]=[C:18]([CH3:17])[N:23]=4)=[O:26])[CH:64]2[CH2:65][CH2:66]3)=[N:59][CH:60]=1

Participants

5

Reactant 4

HCID 593637336-methyl-3-(2H-1,2,3-triazol-2-yl)picolinic acidHCID 670869505-Fluoro-2-(pyrimidin-2-yl)benzoic acidHCID 90411631HCID 90411631, compoundHCID 90411649HCID 90411649, compound

Product 1

HCID 90413409HCID 90413409, compound

Procedure

Prepared analogous to Example 1 substituting 5-fluoro-2-(pyrimidin-2-yl)benzoic acid with 6-methyl-3-(2H-1,2,3-triazol-2-yl)picolinic acid and (1S,2R,4R)-tert-butyl-2-((pyridin-2-yloxy)methyl)-7-azabicyclo[2.2.1]heptane-7-carboxylate with the title compound of Step A. MS (ESI) mass calcd. for C21H21BrN6O2, 468.1; m/z found 469.1, 471.1 [M+H]+. 1H NMR (CDCl3): 8.20 (d, J=2.6 Hz, 0.4H), 8.16 (d, J=2.6 Hz, 0.6H), 8.13 (d, J=8.3 Hz, 0.4H), 8.10 (d, J=8.4 Hz, 0.6H), 7.82-7.77 (m, 2H), 7.64 (dd, J=8.8, 2.6 Hz, 0.4H), 7.60 (dd, J=8.8, 2.6 Hz, 0.6H), 7.33-7.29 (m, 0.4H), 7.22 (d, J=8.4 Hz, 0.6H), 6.69 (d, J=8.8 Hz, 0.4H), 6.50 (d, J=8.8 Hz, 0.6H), 4.84 (dd, J=11.1, 5.2 Hz, 1H), 4.30-4.04 (m, 2H), 3.93-3.85 (m, 1H), 2.62 (s, 1.3H), 2.38-2.17 (m, 2.7H), 2.11-1.95 (m, 1H), 1.94-1.77 (m, 1H), 1.77-1.40 (m, 4H).

Sources & evidence

ORD record
ord-14bc706795524dc7a5a279bef7aef357
Source dataset
uspto-grants-2015_06
Patent number
US09062078B2

Reaction notes

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