4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → HCID 89473226, compound

HRID 931665Notes

Reaction equation

HRID 931665 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[N:12]=[C:11]([O:13][CH3:14])[C:10]3[O:15][C:16]4[C:21]([C@@:22]5([CH2:27][CH2:26][O:25][C:24]([NH2:28])=[N:23]5)[C:9]=3[CH:8]=2)=[CH:20][C:19]([NH2:29])=[CH:18][CH:17]=4)[CH2:3][CH2:2]1.[Cl:30][C:31]1[CH:32]=[CH:33][C:34]([C:37](O)=[O:38])=[N:35][CH:36]=1.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>C1COCC1.CO>[NH2:28][C:24]1[O:25][CH2:26][CH2:27][C@:22]2([C:9]3[CH:8]=[C:7]([C:4]4[CH2:3][CH2:2][O:1][CH2:6][CH:5]=4)[N:12]=[C:11]([O:13][CH3:14])[C:10]=3[O:15][C:16]3[C:21]2=[CH:20][C:19]([NH:29][C:37](=[O:38])[C:34]2[CH:33]=[CH:32][C:31]([Cl:30])=[CH:36][N:35]=2)=[CH:18][CH:17]=3)[N:23]=1

Participants

5

Reactant 3

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 27628725-Chloro-2-picolinic acidHCID 117600333HCID 117600333, compound

Product 1

HCID 89473226HCID 89473226, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of (S)-3-(3,6-dihydro-2H-pyran-4-yl)-1-methoxy-5′,6′-dihydrospiro[chromeno[2,3-c]pyridine-5,4′-[1,3]oxazine]-2′,7-diamine (0.080 g, 0.203 mmol) in THF/MeOH (20.3 mL) were added 5-chloro-2-pyridinecarboxylic acid (0.035 g, 0.223 mmol) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (0.066 g, 0.223 mmol). The resulting reaction mixture was stirred at RT for 2 h. The mixture was quenched with sat. NaHCO3 and extracted with DCM. The combined organic layers were dried over Na2SO4, filtered, concentrated, chromatographed on silica gel using 0-5% MeOH/DCM and repurified by HPLC to afford a white solid as (S)—N-(2′-amino-3-(3,6-dihydro-2H-pyran-4-yl)-1-methoxy-5′,6′-dihydrospiro[chromeno[2,3-c]pyridine-5,4′-[1,3]oxazin]-7-yl)-5-chloropicolinamide (0.0401 g, 0.075 mmol, 37.0% yield).

Workup

  1. customThe resulting reaction mixture
  2. customThe mixture was quenched with sat. NaHCO3
  3. extractionextracted with DCM
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed on silica gel using 0-5% MeOH/DCM
  8. customrepurified by HPLC

Sources & evidence

ORD record
ord-96eef5a03c8d4998b726ad09e013d3cd
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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