Diethyl Ether → HCID 23153488, compound

HRID 492814Notes

Reaction equation

HRID 492814 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([N:16]3[CH2:19][CH2:18][CH2:17]3)=[O:15])[CH:8]=2)=[CH:4][C:3]=1[Cl:22].C(N(CC)CC)C.[F:30][P-](F)(F)(F)(F)F.[N:37]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=2N=N1.C([O:59][CH2:60][CH3:61])C.CN(C)[CH:64]=[O:65]>>[Cl:22][C:3]1[CH:4]=[C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([N:16]3[CH2:19][CH2:18][CH2:17]3)=[O:15])[CH:8]=2)[CH:20]=[CH:21][C:2]=1[NH:1][C:60](=[O:59])[CH2:61][C:64]([NH:37][C:41]1[CH:42]=[CH:43][C:44]([F:30])=[CH:45][CH:40]=1)=[O:65]

Participants

6

Reactant 5

HCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 57677315HCID 57677315, compound

Product 1

HCID 23153488HCID 23153488, compoundYield 81.7%

Procedure

Azetidine-1-carboxylic acid [4-(4-amino-3-chlorophenoxy)pyridin-2-yl]amide (100 mg) was dissolved in N,N-dimethylformamide (2 ml) under a nitrogen atmosphere, and then N-(4-fluorophenyl)malonic acid (186 mg), triethylamine (0.131 ml) and (1H-1,2,3-benzotriazol-1-yloxy)[tri(dimethylamino)]phosphonium hexafluorophosphate (417 mg) were added thereto at 50° C., followed by stirring at the same temperature for 1 hr. The reaction mixture was cooled down to room temperature, and partitioned between ethyl acetate and a 1 N aqueous solution of sodium hydroxide. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, water and brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, to which diethyl ether was added to suspend. The solid was filtered off and dried under aeration to provide the titled compound (128 mg, 81.7%) as pale brown powder.

Workup

  1. customat 50° C.
  2. custompartitioned between ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, water and brine in this order
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customto give a residue
  7. filtrationThe solid was filtered off
  8. customdried under aeration

Sources & evidence

ORD record
ord-b3b9b8c886304486b760005b680b8768
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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