Hydrochloric Acid → HCID 57814611, compound

HRID 1425498Notes

Reaction equation

HRID 1425498 reaction equation
[F:1][C:2]1[CH:10]=[C:9](OC)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:13][C:14]1[CH:30]=[CH:29][C:17]([O:18][CH2:19][CH2:20][NH:21]C(=O)OC(C)(C)C)=[C:16]([C:31]2[N:35]([CH3:36])[N:34]=[CH:33][C:32]=2[Cl:37])[CH:15]=1.CN([C:41]([O:45]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.Cl>ClCCl>[NH2:21][CH2:20][CH2:19][O:18][C:17]1[CH:29]=[CH:30][C:14]([NH:13][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][CH:9]=[C:10]([O:45][CH3:41])[C:2]=2[F:1])=[CH:15][C:16]=1[C:31]1[N:35]([CH3:36])[N:34]=[CH:33][C:32]=1[Cl:37]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27745422-Fluoro-4-methoxybenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67265237HCID 67265237, compound

Product 1

HCID 57814611HCID 57814611, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-fluoro-4-methoxybenzoic acid (92.8 mg, 545 μmol), tert-butyl 2-(4-amino-2-(4-chloro-1-methyl-1H-pyrazol-5-yl)phenoxy)ethylcarbamate (200 mg, 545 μmol), HATU (207 mg, 545 μmol) and triethylamine (76.0 μL, 545 μmol) in dichloromethane was stirred at room temperature overnight. The reaction was diluted with dichloromethane and washed with water. The organic layer was separated, dried over anhydrous Na2SO4, filtered and concentrated. To the crude product was added 2M HCl (5 eq.). The mixture was stirred at room temperature overnight. The mixture was concentrated and the title compound was obtained as a yellow oil. LCMS m/z (%)=419 (M+H, 35Cl, 100), 421 (M+H, 37Cl, 40).

Workup

  1. washwashed with water
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. stirringThe mixture was stirred at room temperature overnight
  7. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-3e3ebd546fdd4bdcbbd5c91223d9a482
Source dataset
uspto-grants-2015_01
Patent number
USRE045337E1

Reaction notes

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