Hydrochloric Acid → HCID 78427514, compound

HRID 880600Notes

Reaction equation

HRID 880600 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]([CH3:41])[C:17]3[N:18]([C:20]([N:25]([C:27]4[S:28][C:29]([C:39]#[N:40])=[C:30]([C:32]5[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=5)[N:31]=4)[CH3:26])=[C:21]([CH2:23][CH3:24])[N:22]=3)[CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.CCOCC>CO>[CH2:23]([C:21]1[N:22]=[C:17]2[C:16]([CH3:41])=[CH:15][C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[CH:19][N:18]2[C:20]=1[N:25]([CH3:26])[C:27]1[S:28][C:29]([C:39]#[N:40])=[C:30]([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[N:31]=1)[CH3:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 90420077HCID 90420077, compound

Product 1

HCID 78427514HCID 78427514, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(3-{[5-Cyano-4-(4-fluoro-phenyl)-thiazol-2-yl]-methyl-amino}-2-ethyl-8-methyl-imidazo[1,2-a]pyridin-6-yl)-piperazine-1-carboxylic acid tert-butyl ester (24.4 g, 42 mmol, 1 eq.) in MeOH (100 mL) was added a 2 M HCl solution in Et2O (127 mL, 254 mmol, 6 eq.). The reaction mixture was stirred at r.t. for 3.5 h then concentrated in vacuo. The residue was partitioned between EtOAc and water. The aqueous layer was extracted twice with EtOAc. A 2 M NaOH solution was added to the aqueous layer until pH reached 8-9 and further extraction with EtOAc was performed. The combined organic layers were then washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The solid was triturated with heptane (100 mL) at r.t. overnight, filtered off, washed with heptane and Et2O, and dried to afford the expected compound.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was partitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted twice with EtOAc
  4. additionA 2 M NaOH solution was added to the aqueous layer until pH
  5. extraction8-9 and further extraction with EtOAc
  6. washThe combined organic layers were then washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe solid was triturated with heptane (100 mL) at r.t. overnight
  11. filtrationfiltered off
  12. washwashed with heptane and Et2O
  13. customdried

Sources & evidence

ORD record
ord-53842c2855ee4b49b482fed21931c35f
Source dataset
uspto-grants-2015_03
Patent number
US08993590B2

Reaction notes

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