Triethylamine → HCID 178425129, compound

HRID 1500995Notes

Reaction equation

HRID 1500995 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([OH:9])[C:3]=1[CH2:10][NH:11][CH3:12].[Cl:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[O:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]2[CH:35]=[CH:34][N:33]=[CH:32][N:31]=2)[C:25]=1[C:36]#[N:37])[C:17](O)=[O:18].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>ClCCl.O>[Cl:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[O:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]2[CH:35]=[CH:34][N:33]=[CH:32][N:31]=2)[C:25]=1[C:36]#[N:37])[C:17]([N:11]([CH2:10][C:3]1[C:4]([OH:9])=[N:5][C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1])[CH3:12])=[O:18]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69672221HCID 69672221, compoundHCID 178482760HCID 178482760, compound

Product 1

HCID 178425129HCID 178425129, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4,6-Dimethyl-3-((methylamino)methyl)pyridin-2-ol (28 mg, 0.17 mmol), 3-chloro-4-(2-cyano-3-(pyrimidin-4-yl)phenoxy)benzoic acid (50 mg, 0.14 mmol), triethylamine (42 mg, 0.42 mmol) and 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (65 mg, 0.17 mmol) in dichloromethane (20 mL) was stirred at room temperature for 15 hours. Water (20 mL) was added to the mixture. The organic phase was separated and concentrated in vacuo to give a residue. The residue was further purified by preparative-HPLC to provide 3-chloro-4-(2-cyano-3-(pyrimidin-4-yl)phenoxy)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-N-methylbenzamide (Compound I-17) as a white solid (34 mg, 49%). LRMS (M+H+) m/z: calcd 499.1. found 499. HPLC purity (214 nm): 94%.

Workup

  1. customThe organic phase was separated
  2. concentrationconcentrated in vacuo
  3. customto give a residue
  4. customThe residue was further purified by preparative-HPLC

Sources & evidence

ORD record
ord-a47860c749c64060bcac341813c9636a
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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