Hydrochloric Acid → HCID 86596440, compound

HRID 584200Notes

Reaction equation

HRID 584200 reaction equation
[F:1][C:2]([F:49])([F:48])[C:3]1[CH:4]=[C:5]([CH:41]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:43]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]#[C:16][C:17]2[CH:18]=[N:19][C:20]([NH:23]C(OC(C)(C)C)=O)=[CH:21][CH:22]=2)[CH2:10][C@H:9]1[CH2:31][C:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[NH:34][CH:33]=1)=[O:7].FC(F)(F)C(O)=O.[ClH:57]>ClCCl.C(OCC)(=O)C>[ClH:57].[ClH:57].[F:47][C:44]([F:45])([F:46])[C:42]1[CH:41]=[C:5]([CH:4]=[C:3]([C:2]([F:48])([F:1])[F:49])[CH:43]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]#[C:16][C:17]2[CH:18]=[N:19][C:20]([NH2:23])=[CH:21][CH:22]=2)[CH2:10][C@H:9]1[CH2:31][C:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[NH:34][CH:33]=1)=[O:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 54131033HCID 54131033, compound

Product 1

HCID 86596440HCID 86596440, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-[(1H-indol-3-yl)methyl]-4-[3-[6-(tert-butoxycarbonylamino)pyridin-3-yl]-2-propynyl]piperazine (127 mg) prepared by a similar manner to that of Example 5-(1) and trifluoroacetic acid (5 ml) in dichloromethane (5 ml) was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between saturated aqueous sodium bicarbonate solution. The organic layer was separated, dried over magnesium sulfate and concentrated under reduced pressure. The syrup obtained was dissolved into ethyl acetate and treated with 4N hydrogen chloride in ethyl acetate to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-[(1H-indol-3-yl) methyl]-4-[3-(6-aminopyridin-3-yl)-2-propynyl]piperazine dihydrochloride (80 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between saturated aqueous sodium bicarbonate solution
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe syrup obtained

Sources & evidence

ORD record
ord-57205eb70dbb48aab8aca67e8e20c690
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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