Trifluoroacetic acid → HCID 68830624, compound

HRID 1787909Notes

Reaction equation

HRID 1787909 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:39]=[C:38]([N:40]3[CH2:44][CH2:43][CH2:42][CH2:41]3)[CH:37]=[CH:36][C:16]=2[C:17]([NH:19][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][C:25]=2[C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][N:30]=2)=[O:27])=[O:18])[CH2:10][CH2:9]1)=O)(C)(C)C.[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48]>C(Cl)Cl.C1(OC)C=CC=CC=1>[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48].[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([NH:28][C:26]([C:25]2[CH:24]=[CH:23][N:22]=[CH:21][C:20]=2[NH:19][C:17](=[O:18])[C:16]2[CH:36]=[CH:37][C:38]([N:40]3[CH2:41][CH2:42][CH2:43][CH2:44]3)=[CH:39][C:15]=2[O:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[O:27])=[N:30][CH:31]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57602450HCID 57602450, compound

Product 1

HCID 68830624HCID 68830624, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

The 3-[2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)benzoylamino]-N-(5-chloropyridin-2-yl)-pyridine-4-carboxamide (109 mg, 0.18 mmol) was dissolved in CH2Cl2 (2 mL) with anisole (1 mL). The solution was treated with trifluoroacetic acid (1 mL) at room temperature for 2 h. The mixture was concentrated to dryness under vacuum, rinsed with hexanes, and sonicated with diethyl ether (5 mL) for 5 min to give 120 mg (0.16 mmol, 89%) of the title product.

Workup

  1. concentrationThe mixture was concentrated to dryness under vacuum
  2. washrinsed with hexanes
  3. customsonicated with diethyl ether (5 mL) for 5 min

Sources & evidence

ORD record
ord-ccc603e9536e469d9837ac6520ce0c29
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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