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

HRID 1050226Notes

Reaction equation

HRID 1050226 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

4

Reactant 3

HCID 661742-Amino-5-chloropyridineHCID 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%.

Workup

  1. custommaterials, preparation

Sources & evidence

ORD record
ord-20c6f70029e440f19edba3c546e62500
Source dataset
uspto-grants-2016_07
Patent number
US09382265B2

Reaction notes

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