Hydrochloric Acid → HCID 86663370, compound

HRID 2069590Notes

Reaction equation

HRID 2069590 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[C:9](/[CH2:39][CH3:40])=[C:10](\[C:26]1[CH:31]=[CH:30][C:29](/[CH:32]=[CH:33]/[C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:28][CH:27]=1)/[C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16](C1CCCCO1)[N:15]=[CH:14]2.Cl>>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[C:9](/[CH2:39][CH3:40])=[C:10](\[C:26]1[CH:31]=[CH:30][C:29](/[CH:32]=[CH:33]/[C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:28][CH:27]=1)/[C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][N:15]=[CH:14]2

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 66794837HCID 66794837, compound

Product 1

HCID 86663370HCID 86663370, compoundYield 164.9%

Conditions

Temperature
80 °C

Procedure

A round-bottom flask equipped with a magnetic stir bar was charged with (E)-ethyl 3-(4-((E)-2-(2-chloro-4-fluorophenyl)-1-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)but-1-en-1-yl)phenyl)acrylate (255.9 g, 457.8 mmol) and a solution of HCl (732 mL, 1.25 M in ethyl alcohol). The reaction was heated at 80° C. for 2.5 h, allowed to cool to room temperature, and then concentrated to an orange gel. tert-Butyl methyl ether (2.3 L) was added. After stirring for 5 min, solids began to precipitate. The mixture was stirred at room temperature for 2 h and then filtered. The solids were washed with MTBE (700 mL) and dried to give the title compound (193 g) as an off-white solid. 1H NMR (DMSO-d6): δ 8.11 (s, 1H), 7.69 (s, 1H), 7.57-7.50 (m, 2H), 7.45-7.33 (m, 4H), 7.21-7.10 (m, 2H), 6.96 (d, 2H), 6.48 (d, 1H), 4.14 (q, 2H), 2.38 (q, 2H), 1.19 (t, 3H), 0.90 (t, 3H); LCMS: 475 (M+H)+.

Workup

  1. customA round-bottom flask equipped with a magnetic stir bar
  2. temperatureto cool to room temperature
  3. concentrationconcentrated to an orange gel
  4. additiontert-Butyl methyl ether (2.3 L) was added
  5. customto precipitate
  6. stirringThe mixture was stirred at room temperature for 2 h
  7. filtrationfiltered
  8. washThe solids were washed with MTBE (700 mL)
  9. customdried

Sources & evidence

ORD record
ord-bd67dd83fec6443698a9e4809974c866
Source dataset
uspto-grants-2012_10
Patent number
US08299112B2

Reaction notes

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