Hydrochloric Acid → HCID 178479508, compound

HRID 1048729Notes

Reaction equation

HRID 1048729 reaction equation
C(OC([NH:8][C:9]([NH:11][C:12](=[O:34])[CH2:13][O:14][CH2:15][C:16]1[N:17]=[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]2[C:24]=1[C:25]#[C:26][C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)=[NH:10])=O)(C)(C)C.[ClH:35]>C(O)C.O1CCOCC1>[ClH:35].[C:9]([NH:11][C:12](=[O:34])[CH2:13][O:14][CH2:15][C:16]1[N:17]=[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]2[C:24]=1[C:25]#[C:26][C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)(=[NH:8])[NH2:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 140678680HCID 140678680, compound

Product 1

HCID 178479508HCID 178479508, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

190 mg (0.408 mmol) of N—(N-(tert-butoxycarbonyl)carbamimidoyl)-2-((3-((4-fluorophenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl)methoxy)acetamide were dissolved in 2 ml of ethanol before adding 1.020 ml (4.08 mmol) of a 4N hydrochloric acid solution in dioxane. The solution was heated to 60° C. for 2 h. The solvent was evaporated in vacuo. By cooling, the crystallised solid was filtered and washed with ethanol. 85 mg (yield=52%) of N-carbamimidoyl-2-((3-((4-fluorophenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl) methoxy)acetamide hydrochloride were obtained as a yellow solid. LC-MS: m/z=366 (MH+) UV purity at 254 nm=99%. 1H NMR (300 MHz, DMSO) δ 11.36 (s, 1H), 8.86 (d, J=6.7 Hz, 1H), 8.55 (d, J=28.4 Hz, 4H), 7.92-7.71 (m, 4H), 7.44-7.31 (m, 3H), 4.99 (s, 2H), 4.40 (s, 2H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. temperatureBy cooling
  3. filtrationthe crystallised solid was filtered
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-25379646d8fe4b38b4770a644bcc3b4c
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

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