Chloride → HCID 68548133, compound

HRID 1446704Notes

Reaction equation

HRID 1446704 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[C:4]([F:12])[CH:3]=1.[CH3:13][C:14]1([C:17]2[S:21][C:20]([NH2:22])=[N:19][N:18]=2)[CH2:16][CH2:15]1.CN1CCOCC1.COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.[Cl-]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:22][C:20]2[S:21][C:17]([C:14]3([CH3:13])[CH2:16][CH2:15]3)=[N:18][N:19]=2)=[O:11])=[C:4]([F:12])[CH:3]=1

Participants

7

Reactant 5

HCID 312ChlorideHCID 79724-MethylmorpholineHCID 27340604-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-iumHCID 140537922-(4-Bromo-2-fluorophenyl)acetic acidHCID 45123408HCID 45123408, compound

Product 1

HCID 68548133HCID 68548133, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine (4-bromo-2-fluoro-phenyl)-acetic acid (3.81 g, 16.35 mmol) and 5-(1-Methyl-cyclopropyl)-[1,3,4]thiadiazol-2-ylamine (2.54 g, 16.35 mmol) in THF (45 mL). Under N2, add 4-methyl-morpholine (2.16 mL, 19.62 mmol), then 4-(4,6-dimethoxy-[1,3,5]triazin-2-yl)-4-methyl-morpholin-4-ium; chloride (5.43 g, 19.62 mmol). Stir the reaction mixture for 14 hours under N2. Extract with ethyl acetate versus water. Wash with aqueous saturated sodium chloride, dry over magnesium sulfate, filter, and concentrate. Triturate the resulting solid from ethyl acetate/hexanes, filter, and dry to give fluffy white solid as the title compound (2.86 g, 47%). MS (ES), mm/z 370, 372 (M+1).

Workup

  1. extractionExtract with ethyl acetate versus water
  2. washWash with aqueous saturated sodium chloride
  3. dry with materialdry over magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customTriturate the resulting solid from ethyl acetate/hexanes
  7. filtrationfilter
  8. customdry

Sources & evidence

ORD record
ord-c4024db548664e2fb4ec338d034ed0dd
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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