Methyl iodide → HCID 86636300, compound

HRID 541960Notes

Reaction equation

HRID 541960 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]3C=C[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]C1.[CH:44](N(CC)C(C)C)(C)C.CI>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([O-:12])=[O:11].[Cl:15][C:16]1[CH:17]=[N:18][C:19]2[NH:20][C:21]3[CH:43]=[CH:25][CH:24]=[C:3]([CH:2]=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[CH2:10][CH2:9][N+:40]([CH3:39])([CH3:44])[CH2:41][CH2:42]1.[Cl:15][C:16]1[CH:17]=[N:18][C:19]2[NH:20][C:21]3[CH:43]=[CH:25][CH:24]=[C:3]([CH:2]=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[CH2:10][CH2:9][N+:40]([CH3:39])([CH3:44])[CH2:41][CH2:42]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 86636299HCID 86636299, compound

Product 1

HCID 86636300HCID 86636300, compoundYield 128.1%

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) (20 mg, 32 μmol) and N,N-diisopropylethylamine (27 μL, 0.16 mmol) in dichloromethane (0.3 mL) was treated with methyl iodide (10 μL, 0.16 mmol) and stirred for 16 h. The reaction mixture was purified by preparative LCMS to give the desired product (15 mg, 72%) as a solid. LCMS for C24H28ClN6 (M)+: m/z=435.1. 1H NMR (400 MHz, DMSO-d6): δ 9.41 (s, 1H), 9.17 (s, 1H), 8.11 (s, 1H), 7.98 (s, 1H), 7.81 (d, J=2.3 Hz, 1H), 7.30 (d, J=8.6 Hz, 1H), 7.11-7.07 (m, 2H), 6.87 (d, J=9.2 Hz, 1H), 6.79 (d, J=7.4 Hz, 1H), 3.55-3.53 (m, 4H), 3.22 (s, 6H), 3.15 (br s, 4H), 2.95-2.90 (m, 4H).

Workup

  1. customThe reaction mixture was purified by preparative LCMS

Sources & evidence

ORD record
ord-7433d86f33964fd8a61f9421b658149a
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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