Trifluoroacetic acid → HCID 86636368, compound

HRID 542035Notes

Reaction equation

HRID 542035 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[NH:6][C:7]3[CH:8]=[C:9]([CH2:25][N:26]4[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]4)[CH:10]=[C:11]([CH:24]=3)[CH2:12][CH2:13][O:14][C:15]3[CH:23]=[C:19]([NH:20][C:21]=1[N:22]=2)[CH:18]=[CH:17][CH:16]=3.[C:39]([OH:45])([C:41]([F:44])([F:43])[F:42])=[O:40]>>[F:42][C:41]([F:44])([F:43])[C:39]([OH:45])=[O:40].[F:42][C:41]([F:44])([F:43])[C:39]([OH:45])=[O:40].[F:42][C:41]([F:44])([F:43])[C:39]([OH:45])=[O:40].[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[NH:6][C:7]3[CH:8]=[C:9]([CH2:25][N:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)[CH:10]=[C:11]([CH:24]=3)[CH2:12][CH2:13][O:14][C:15]3[CH:23]=[C:19]([NH:20][C:21]=1[N:22]=2)[CH:18]=[CH:17][CH:16]=3

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57962369HCID 57962369, compound

Product 1

HCID 86636368HCID 86636368, compoundYield 32%

Procedure

A solution of tert-butyl 4-{[6-chloro-14-oxa-2,4,8,23-tetraazatetracyclo[15.3.1.1(3,7).1(9,13)]tricosa-1(21),3(23),4,6,9(22),10,12,17,19-nonaen-19-yl]methyl}piperazine-1-carboxylate in TFA (1.5 mL) was stirred at 20° C. for 15 min, concentrated, and purified by preparative LCMS to give the desired product (15 mg, 32% for 2 steps) as a white solid. LCMS for C23H26ClN6O (M+H)+: m/z=437.0.

Workup

  1. concentrationconcentrated
  2. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-856edd55edd74d95b13b0a248a1989be
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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