Diisopropylethylamine → HCID 90204273, compound

HRID 1480285Notes

Reaction equation

HRID 1480285 reaction equation
[CH:1]1([C:4]2[C:5]([O:13][CH2:14][C:15]3([CH3:19])[CH2:18][O:17][CH2:16]3)=[CH:6][C:7]([C:10]([OH:12])=O)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.[C:47]1([C:53]2[O:57][C:56]([C:58]([NH2:61])([CH3:60])[CH3:59])=[N:55][N:54]=2)[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>ClCCl>[CH:1]1([C:4]2[C:5]([O:13][CH2:14][C:15]3([CH3:19])[CH2:18][O:17][CH2:16]3)=[CH:6][C:7]([C:10]([NH:61][C:58]([C:56]3[O:57][C:53]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)=[N:54][N:55]=3)([CH3:60])[CH3:59])=[O:12])=[N:8][CH:9]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 12434883HCID 12434883, compoundHCID 90203786HCID 90203786, compound

Product 1

HCID 90204273HCID 90204273, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the acid 5-cyclopropyl-4-((3-methyloxetan-3-yl)methoxy)picolinic acid (20 mg, 76.0 μmol) in dichloromethane (1 ml) was added DIPEA (24.5 mg, 33.2 μl, 190 μmol) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium chloride (23.1 mg, 83.6 μmol). The reaction is stirred for 30 minutes at room temperature followed by addition of 2-(5-phenyl-1,3,4-oxadiazol-2-yl)propan-2-amine (CAN 68176-04-5, 15.4 mg, 76.0 μmol) and the reaction mixture was stirred overnight at room temperature. The reaction was diluted with dichloromethane (5 mL) and washed with a 0.2M aqueous solution of hydrochloric acid (3×10 mL) and brine (15 mL). The organic phase is dried over magnesium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a gradient of heptane and ethyl acetate to yield the title compound (24.3 mg, 71%). MS (ESI, m/z): 449.7 (M+H+).

Workup

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. washwashed with a 0.2M aqueous solution of hydrochloric acid (3×10 mL) and brine (15 mL)
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customevaporated down to dryness
  5. customThe crude material was purified by flash chromatography on silica eluting with a gradient of heptane and ethyl acetate

Sources & evidence

ORD record
ord-02a847b568554957999900f7759c65c9
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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