HCID 86636302, compound → HCID 86636301, compound

HRID 541961Notes

Reaction equation

HRID 541961 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].C([NH:19][C:20]([N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:29]=[CH:30][C:31]3[NH:32][C:33]4[N:49]=[C:37]([NH:38][C:39]5[CH:40]=[CH:41][CH:42]=[C:43]([CH:48]=5)[CH2:44][CH2:45][C:46]=2[CH:47]=3)[N:36]=[CH:35][C:34]=4[Cl:50])[CH2:24][CH2:23]1)=[O:21])(C)(C)C>FC(F)(F)C(O)=O>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[Cl:50][C:34]1[CH:35]=[N:36][C:37]2[NH:38][C:39]3[CH:40]=[CH:41][CH:42]=[C:43]([CH:48]=3)[CH2:44][CH2:45][C:46]3[CH:47]=[C:31]([NH:32][C:33]=1[N:49]=2)[CH:30]=[CH:29][C:28]=3[N:25]1[CH2:26][CH2:27][N:22]([C:20]([NH2:19])=[O:21])[CH2:23][CH2:24]1

Participants

3

Reactant 1

HCID 86636302HCID 86636302, compound

Product 1

HCID 86636301HCID 86636301, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N-(tert-butyl)-4-[6-chloro-2,4,8,22-tetraazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaen-12-yl]piperazine-1-carboxamide bis(trifluoroacetate) (12 mg, 16 μmol) in trifluoroacetic acid (1 mL) was stirred at 20° C. for 4 h. The reaction mixture was purified by preparative LCMS to give the desired product (8 mg, 72%) as a solid. LCMS for C23H25ClN7O (M+H)+: m/z=450.0. 1H NMR (300 MHz, CD3OD): δ 8.09 (s, 1H), 7.74-7.69 (m, 2H), 7.22-7.11 (m, 2H), 7.04-7.00 (m, 2H), 6.87 (d, J=7.9 Hz, 1H), 3.60 (br s, 4H), 3.14 (s, 4H), 2.89-2.87 (m, 4H).

Workup

  1. customThe reaction mixture was purified by preparative LCMS

Sources & evidence

ORD record
ord-94de48a0edf74683822a2f952082315d
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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