Triethylamine → HCID 178454362, compound

HRID 81257Notes

Reaction equation

HRID 81257 reaction equation
[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])(=[O:4])[NH:2][NH2:3].C(N(CC)CC)C.CO[C:19]([C:21]1[N:26]=[C:25]([C:27]2[CH:28]=[N:29][CH:30]=[C:31]([Cl:33])[CH:32]=2)[C:24]2[N:34]([CH2:44][C@H:45]3[CH2:50][CH2:49][C@H:48]([CH3:51])[CH2:47][CH2:46]3)[C:35]([N:37]3[CH2:41][CH2:40][CH2:39][C@H:38]3[CH2:42][F:43])=[N:36][C:23]=2[CH:22]=1)=[NH:20]>C(O)C.CCOC(C)=O>[Cl:33][C:31]1[CH:32]=[C:27]([C:25]2[C:24]3[N:34]([CH2:44][C@H:45]4[CH2:50][CH2:49][C@H:48]([CH3:51])[CH2:47][CH2:46]4)[C:35]([N:37]4[CH2:41][CH2:40][CH2:39][C@H:38]4[CH2:42][F:43])=[N:36][C:23]=3[CH:22]=[C:21]([C:19](=[NH:20])[NH:3][NH:2][C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[N:26]=2)[CH:28]=[N:29][CH:30]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 70091tert-Butyl carbazateHCID 178496778HCID 178496778, compound

Product 1

HCID 178454362HCID 178454362, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tert-butyl carbazate (106 mg, 0.802 mmol) and triethylamine (418 μL, 3.006 mmol) were added to a solution of crude methyl-4-(5-chloropyridin-3-yl)-2-[(2S)-2-(fluoromethyl)pyrrolidin-1-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridin-6-carbimidate (Example 14.2, Step 1; 50 mg, 0.100 mmol) in ethanol (100 μL) in a vial, and the reaction was capped and stirred at ambient temperature for 72 hr. The reaction was diluted with EtOAc and washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated to afford crude tert-butyl 2-((4-(5-chloropyridin-3-yl)-2-((S)-2-(fluoromethyl)pyrrolidin-1-yl)-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridin-6-yl)(imino)methyl)hydrazinecarboxylate. MS ESI calc'd. for C30H40ClFN8O2 [M+H]+ 599. found 599. This material was taken on to Step 2 without further purification.

Workup

  1. customwas capped
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cc5f47e10ff0415fab686d5794b6f079
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

Loading…