5-Chloro-2-picolinic acid → HCID 131736052, compound

Reaction equation

[NH2:1][CH2:2][C@H:3]1[C@H:11]2[N:6]([C:7]3[CH:15]=[CH:14][C:13]([N:16]4[CH2:21][CH2:20][O:19][CH2:18][C:17]4=[O:22])=[CH:12][C:8]=3[O:9][CH2:10]2)[C:5](=[O:23])[O:4]1.[Cl:24][C:25]1[CH:26]=[CH:27][C:28]([C:31](O)=O)=[N:29][CH:30]=1.CN([C:37]([O:41]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[Cl:24][C:25]1[CH:26]=[CH:27][C:28]([CH2:31][C:37]([NH:1][CH2:2][C@H:3]2[C@H:11]3[N:6]([C:7]4[CH:15]=[CH:14][C:13]([N:16]5[CH2:21][CH2:20][O:19][CH2:18][C:17]5=[O:22])=[CH:12][C:8]=4[O:9][CH2:10]3)[C:5](=[O:23])[O:4]2)=[O:41])=[N:29][CH:30]=1

Participants

Reactant 3

HCID 27628725-Chloro-2-picolinic acid

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

HCID 90295505HCID 90295505, compound

Product 1

HCID 131736052HCID 131736052, compoundYield 85.85%

Procedure

Using compound (3S,3 aS)-3-aminomethyl-7-(3-oxomorpholin-4-yl)-3a,4-dihydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-1 (3H)-one (60 mg, 0.188 mmol) (the product of step (e) in Example 1), 5-chloropyridin-2-carboxylic acid (36 mg, 0.225 mmol), HATU (107 mg, 0.282 mmol), and TEA (38 mg, 0.376 mmol) as starting materials, preparation following the method as described in Example 11 (g) afforded white solid compound 74 mg, yield: 85.85%.