Triethylamine → HCID 86590726, compound

HRID 1793052Notes

Reaction equation

HRID 1793052 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:18]([F:19])=[C:17]([F:20])[CH:16]=[CH:15][C:11]=2[C:12]([OH:14])=O)=[C:5]([F:21])[CH:4]=1)[CH3:2].CC1(C)O[C@H](CNO)CO1.[CH3:32][C:33]1([CH3:42])[O:38][C@@H:37]([CH2:39][O:40][NH2:41])[CH2:36]C[O:34]1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>ClCCl>[CH3:42][C:33]1([CH3:32])[O:38][C@@H:37]([CH2:39][O:40][NH:41][C:12](=[O:14])[C:11]2[CH:15]=[CH:16][C:17]([F:20])=[C:18]([F:19])[C:10]=2[NH:9][C:6]2[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][C:5]=2[F:21])[CH2:36][O:34]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 2724699PyBOPHCID 220256532-[(4-Ethyl-2-fluorophenyl)amino]-3,4-difluorobenzoic acidHCID 23541087(S)-(+)-2,2-Dimethyl-4-hydroxyaminomethyl-1,3-dioxolaneHCID 69628065(R)-O-(2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-hydroxylamine

Product 1

HCID 86590726HCID 86590726, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of the product of Example 1, Step D, 2-[(4-ethyl-2-fluorophenyl)amino]-3,4-difluorobenzoic acid (0.480 g, 1.626 mmol) in dichloromethane (25 mL) is added to the product of Example 31, Step D, (R)—O-(2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-hydroxylamine (0.38 g, 2.57 mmol), triethylamine (0.54 mL, 3.85 mmol), and benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate (1.34 g, 2.57 mmol) and allowed to stir at ambient temperature for 90 minutes. The reaction mixture was concentrated in vacuo and the affording residue was partitioned between ethyl acetate and water. The organic layers were washed twice with saturated sodium carbonate solution and twice with brine. The organic layer was collected, dried over sodium sulfate, filtered and concentrated in vacuo. N-((R)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-2-(4-ethyl-2-fluoro-phenylamino)-3,4-difluoro-benzamide was isolated via silica column chromatography in 4:1 hexanes/ethyl acetate, then 3:1 hexanes/ethyl acetate affording a white foam (0.515 g, 56.7%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe affording residue was partitioned between ethyl acetate and water
  3. washThe organic layers were washed twice with saturated sodium carbonate solution and twice with brine
  4. customThe organic layer was collected
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8f5b4bb3d9eb4f009cf884288ecb6d46
Source dataset
uspto-grants-2006_07
Patent number
US07078438B2

Reaction notes

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