Hydrochloric Acid → HCID 68294845, compound

HRID 1850049Notes

Reaction equation

HRID 1850049 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:33]=[C:34]([F:36])[CH:35]=1)[O:6][CH2:7][CH2:8][N:9]1[CH:13]=[C:12](/[CH:14]=[CH:15]/[C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[NH:25]C(=O)OC(C)(C)C)=[O:17])[CH:11]=[N:10]1>O1CCOCC1.CCOC(C)=O>[NH2:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[NH:18][C:16](=[O:17])/[CH:15]=[CH:14]/[C:12]1[CH:11]=[N:10][N:9]([CH2:8][CH2:7][O:6][C:5]2[CH:33]=[C:34]([F:36])[CH:35]=[C:3]([Cl:2])[CH:4]=2)[CH:13]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86702813HCID 86702813, compound

Product 1

HCID 68294845HCID 68294845, compoundYield 107.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A 4 M solution of HCl in dioxane (2 mL) was added to a solution of (E)-tert-butyl (2-(3-(1-(2-(3-chloro-5-fluorophenoxy)ethyl)-1H-pyrazol-4-yl)acrylamido)phenyl)carbamate (118 mg, 0.23 mmol) in dioxane (3 mL) and the mixture was stirred for 6 h at room temperature under a nitrogen atmosphere. The reaction mixture was then diluted with EtOAc (15 mL). The salt was filtered, washed with EtOAc and dried overnight to give 99 mg of the hydrochloric acid salt of (E)-N-(2-aminophenyl)-3-(1-(2-(3-chloro-5-fluorophenoxy)ethyl)-1H-pyrazol-4-yl)acrylamide as an off-white solid. MS: ES+(M+Na)+: 423

Workup

  1. filtrationThe salt was filtered
  2. washwashed with EtOAc
  3. customdried overnight

Sources & evidence

ORD record
ord-b709bed440c44349be4cf96d33f6c25b
Source dataset
uspto-grants-2015_02
Patent number
US08957066B2

Reaction notes

Loading…