2-Amino-5-chloropyridine → HCID 90295622, compound

Reaction equation

[O:1]=[C:2]1[N:6]2[C:7]3[CH:14]=[CH:13][C:12]([N:15]4[CH2:20][CH2:19][O:18][CH2:17][C:16]4=[O:21])=[CH:11][C:8]=3[O:9][CH2:10][C@H:5]2[C@H:4]([C:22]([OH:24])=O)[O:3]1.[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([NH2:32])=[N:30][CH:31]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([NH:32][C:22]([C@H:4]2[C@H:5]3[N:6]([C:7]4[CH:14]=[CH:13][C:12]([N:15]5[CH2:20][CH2:19][O:18][CH2:17][C:16]5=[O:21])=[CH:11][C:8]=4[O:9][CH2:10]3)[C:2](=[O:1])[O:3]2)=[O:24])=[N:30][CH:31]=1

Participants

Reactant 3

HCID 661742-Amino-5-chloropyridine

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

HCID 90295836HCID 90295836, compound

Product 1

HCID 90295622HCID 90295622, compoundYield 52.65%

Procedure

Using compound (3R,3aS)-1-oxo-7-(3-oxomorpholin-4-yl)-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-carboxylic acid (the product of step (b) in Example 36) (90 mg, 0.24 mmol), 5-chloropyridine-2-amine (37 mg, 0.287 mmol), HATU (137 mg, 0.36 mmol), and TEA (48.4 mg, 0.48 mmol) as starting materials, preparation following the method as described in Example 11 (g) afforded white solid 56 mg, yield: 52.65%.