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

HRID 1050211Notes

Reaction equation

HRID 1050211 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

4

Reactant 3

HCID 27628725-Chloro-2-picolinic acidHCID 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%.

Workup

  1. custommaterials, preparation

Sources & evidence

ORD record
ord-e10ebf703b52470491fbcabe64ee0959
Source dataset
uspto-grants-2016_07
Patent number
US09382265B2

Reaction notes

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