Hydrochloric Acid → HCID 53328240, compound

HRID 518012Notes

Reaction equation

HRID 518012 reaction equation
CCN=C=NCCCN(C)C.[CH3:12][N:13]([CH3:18])[CH2:14][C:15](O)=[O:16].[CH3:19][N:20]1[C:28]2[CH:27]=[C:26]([C:29]3[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][CH2:37][NH:38][CH3:39])=[C:31]([C:40]([F:43])([F:42])[F:41])[CH:30]=3)[N:25]=[C:24]([C:44]#[N:45])[C:23]=2[N:22]=[N:21]1.Cl>C1COCC1.C(OCC)(=O)C.C(N(CC)CC)C>[C:44]([C:24]1[C:23]2[N:22]=[N:21][N:20]([CH3:19])[C:28]=2[CH:27]=[C:26]([C:29]2[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][CH2:37][N:38]([CH3:39])[C:15](=[O:16])[CH2:14][N:13]([CH3:18])[CH3:12])=[C:31]([C:40]([F:41])([F:43])[F:42])[CH:30]=2)[N:25]=1)#[N:45]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 673N,N-DimethylglycineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 70945143HCID 70945143, compound

Product 1

HCID 53328240HCID 53328240, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

EDCI (290 mg) was added to the mixture of 2-(dimethylamino)acetic acid (155 mg), methyl-6-(4-(3-(methylamino)propyl)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]-triazolo[4,5-c]pyridine-4-carbonitrile, triethylamine (0.5 ml) in THF (5 ml). The mixture was stirred at rt for 5 hours, then diluted with ethyl acetate (100 ml), washed with sodium bicarbonate (50 ml), brine (50 ml), dried over sodium sulphate, solvent removed, residue dissolved in MeOH/NMP (3:1, 6 ml), and purified by basic hplc to give free base which was then converted to HCl salt as usual (70 mg). 1H NMR (CD3OD) δ: 8.68 (s, 1H), 8.5 (s, 1H), 8.46 (d, 1H), 7.65 (d, 1H), 4.47 (s, 3H), 4.27 (s, 2H), 3.60 (t, 2H), 3.04 (s, 3H), 2.96 (s, 6H), 2.90 (t, 2H), 1.95 (m, 2H). MS m/z 460 (M+H).

Workup

  1. washwashed with sodium bicarbonate (50 ml), brine (50 ml)
  2. dry with materialdried over sodium sulphate, solvent
  3. customremoved
  4. dissolutionresidue dissolved in MeOH/NMP (3:1, 6 ml)
  5. custompurified by basic hplc
  6. customto give free base which

Sources & evidence

ORD record
ord-e3e44717ae49422b8bbe982b19aed6ad
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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