Hydrochloric Acid → HCID 73671792, compound

HRID 2275873Notes

Reaction equation

HRID 2275873 reaction equation
Cl.C(OCC)C.[F:7][C:8]1[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[C:9]=1[CH2:10][O:11][C:12]1[C:13]2[N:14]([C:18]([C:22]([NH:24][CH:25]([C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=3)[CH2:26][NH:27]C(=O)OC(C)(C)C)=[O:23])=[C:19]([CH3:21])[N:20]=2)[CH:15]=[CH:16][CH:17]=1>>[NH2:27][CH2:26][CH:25]([NH:24][C:22]([C:18]1[N:14]2[CH:15]=[CH:16][CH:17]=[C:12]([O:11][CH2:10][C:9]3[C:42]([F:46])=[CH:43][CH:44]=[CH:45][C:8]=3[F:7])[C:13]2=[N:20][C:19]=1[CH3:21])=[O:23])[C:35]1[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 90136003HCID 90136003, compound

Product 1

HCID 73671792HCID 73671792, compound

Procedure

7 ml of 2M hydrochloric acid in diethyl ether (14 mmol) were added to 363 mg of tert-butyl {2-[({8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}-carbonyl)amino]-2-(4-fluorophenyl)ethyl}carbamate (Example 79A, 0.63 mmol), and the mixture was stirred at RT for 3 h. The resulting precipitate was filtered off, washed with diethyl ether, dissolved in dichloromethane and methanol and washed with saturated aqueous sodium bicarbonate solution. The organic phase was dried over sodium sulphate and filtered and the filtrate was concentrated and dried under high vacuum. This gave 275 mg of the title compound (96% of theory).

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. washwashed with diethyl ether
  3. dissolutiondissolved in dichloromethane
  4. washmethanol and washed with saturated aqueous sodium bicarbonate solution
  5. dry with materialThe organic phase was dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-152b366cfb5c4ed7b5dbcb7ec5c6e6cc
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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