Hydrogen chloride-ethyl acetate → HCID 58851578, compound

HRID 1696515Notes

Reaction equation

HRID 1696515 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]#[N:21])[CH:15]=2)=[O:12])[N:7]([C:22]2[CH:31]=[C:30]3[C:25]([CH2:26][CH2:27][N:28](C(OC(C)(C)C)=O)[CH2:29]3)=[CH:24][CH:23]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.CCOC(C)=O>CCOC(C)=O.CCOCC>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]#[N:21])[CH:15]=2)=[O:12])[N:7]([C:22]2[CH:31]=[C:30]3[C:25]([CH2:26][CH2:27][NH:28][CH2:29]3)=[CH:24][CH:23]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 67271705HCID 67271705, compound

Product 1

HCID 58851578HCID 58851578, compoundYield 50.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
22.5 °C

Procedure

To t-butyl 7-(3-t-butyl-5-(3-(3-cyanophenyl)ureido)-1H-pyrazol-1-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (0.34 g, 0.66 mmol) in EtOAc (5.0 ml) was added 3M HCl/EtOAc (1.1 mL, 3.3 mmol). The resulting mixture was stirred at 20-25° C. for 6.5 h. The suspension was diluted with Et2O to fully precipitate the solids. These were collected by filtration, rinsed with Et2O and dried to yield 1-(3-t-butyl-1-(1,2,3,4-tetrahydroisoquinolin-7-yl)-1H-pyrazol-5-yl)-3-(3-cyanophenyl)urea (0.1377 g, 46% yield) of as an off-white solid. 1H NMR (400 MHz, DMSO-d6): 10.1 (s, 1H), 9.47 (brs, 2H), 8.97 (s, 1H), 7.94-7.93 (m, 1H), 7.63-7.60 (m, 1H), 7.49-7.33 (m, 5H), 6.37 (s, 1H), 4.36 (brs, 2H), 3.37 (brs, 2H), 3.06-3.03 (m, 2H), 1.28 (s, 9H); MS (ESI) m/z: 415.3 (M+H+).

Workup

  1. customto fully precipitate the solids
  2. filtrationThese were collected by filtration
  3. washrinsed with Et2O
  4. customdried

Sources & evidence

ORD record
ord-bc765c0e304249128c00178ffd4703e2
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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