3-Hydroxybenzoic Acid → HCID 86758852, compound

HRID 1060885Notes

Reaction equation

HRID 1060885 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[CH3:11][S:12](Cl)(=[O:14])=[O:13].C(N(CC)CC)C.Cl.Cl.[NH2:25][CH2:26][CH2:27][C:28]([NH:30][C:31]([C:39]1[CH:44]=[CH:43][C:42]([C:45]#[N:46])=[C:41]([F:47])[CH:40]=1)([C:33]1[N:34]([CH3:38])[CH:35]=[N:36][CH:37]=1)[CH3:32])=[O:29]>C(Cl)Cl.O>[C:45]([C:42]1[CH:43]=[CH:44][C:39]([C:31]([NH:30][C:28]([CH2:27][CH2:26][NH:25][C:5]([C:4]2[CH:3]=[C:2]([O:1][S:12]([CH3:11])(=[O:14])=[O:13])[CH:10]=[CH:9][CH:8]=2)=[O:7])=[O:29])([C:33]2[N:34]([CH3:38])[CH:35]=[N:36][CH:37]=2)[CH3:32])=[CH:40][C:41]=1[F:47])#[N:46]

Participants

7

Reactant 4

HCID 74203-Hydroxybenzoic AcidHCID 8471Triethylamine2×HCID 31297Methanesulfonyl chlorideHCID 18629449HCID 18629449, compound

Product 1

HCID 86758852HCID 86758852, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-hydroxybenzoic acid (0.07 g, 0.51 mmol), methanesulfonyl chloride(0.15 g, 1.29 mmol), and triethylamine (0.16g, 1.54 mmol) in CH2Cl2 (3 mL) was stirred for 1 hr at 0° C. The reaction was allowed to come to room temperature and 3-amino-N-[1-(4-cyano-3-fluoro-phenyl)-1-(3-methyl-3H-imidazol-4-yl)-ethyl]-propionamide dihydrochloride and triethylamine (0.10 g, 1.03 mmol) were added. After stirring overnight, H2O (1 mL) was added and the mixture was extracted with CH2Cl2 (3×5 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo to provide the title compound.

Workup

  1. customto come to room temperature
  2. extractionthe mixture was extracted with CH2Cl2 (3×5 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-47c4dcd255294386b6aa4e7b86643aa7
Source dataset
uspto-grants-2003_02
Patent number
US06525074B2

Reaction notes

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