Benzoyl chloride → HCID 86636309, compound

HRID 541968Notes

Reaction equation

HRID 541968 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].[Cl:15][C:16]1[CH:17]=[N:18][C:19]2[NH:20][C:21]3[CH:22]=[CH:23][CH:24]=[C:25]([CH:43]=3)[CH2:26][CH2:27][C:28]3[CH:36]=[C:32]([NH:33][C:34]=1[N:35]=2)[CH:31]=[CH:30][C:29]=3[N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1.C(N(CC)C(C)C)(C)C.[C:53](Cl)(=[O:60])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>ClCCl>[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:53]([N:40]1[CH2:41][CH2:42][N:37]([C:29]2[CH:30]=[CH:31][C:32]3[NH:33][C:34]4[N:35]=[C:19]([NH:20][C:21]5[CH:22]=[CH:23][CH:24]=[C:25]([CH:43]=5)[CH2:26][CH2:27][C:28]=2[CH:36]=3)[N:18]=[CH:17][C:16]=4[Cl:15])[CH2:38][CH2:39]1)(=[O:60])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 86636299HCID 86636299, compound

Product 1

HCID 86636309HCID 86636309, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-chloro-12-piperazin-1-yl-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-nonaene bis(trifluoroacetate) (30 mg, 47 μmol) and N,N-diisopropylethylamine (41 μL, 0.24 mmol) in dichloromethane was treated with benzoyl chloride (11 μL, 95 μmol) and stirred for 16 h. The reaction mixture was purified by preparative LCMS to give the desired product (14 mg, 40%) as a solid. LCMS for C29H27ClN6O (M+H)+: m/z=511.1. 1H NMR (400 MHz, DMSO-d6): δ 9.54 (br s, 1H), 9.38 (br s, 1H), 8.14 (s, 1H), 7.94 (s, 1H), 7.77 (d, J=2.3 Hz, 1H), 7.47-7.43 (m, 4H), 7.12-7.02 (m, 3H), 6.87-6.82 (m, 2H), 3.79 (br s, 2H), 3.49 (br s, 2H), 2.97 (s, 4H), 2.87-2.79 (m, 4H).

Workup

  1. customThe reaction mixture was purified by preparative LCMS

Sources & evidence

ORD record
ord-48d1dc43feb54470a0b4d21429b08431
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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