Acetyl chloride → HCID 66896724, compound

HRID 541578Notes

Reaction equation

HRID 541578 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:10]=[N:11][C:12]2[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[C:18]([CH:40]=3)[CH2:19][CH2:20][C:21]3[CH:29]=[C:25]([NH:26][C:27]=1[N:28]=2)[CH:24]=[CH:23][C:22]=3[O:30][CH2:31][C:32](=[O:39])[N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1.C(N(CC)C(C)C)(C)C.[C:50](Cl)(=[O:52])[CH3:51]>CN(C)C=O>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:50]([N:36]1[CH2:37][CH2:38][N:33]([C:32](=[O:39])[CH2:31][O:30][C:22]2[CH:23]=[CH:24][C:25]3[NH:26][C:27]4[N:28]=[C:12]([NH:13][C:14]5[CH:15]=[CH:16][CH:17]=[C:18]([CH:40]=5)[CH2:19][CH2:20][C:21]=2[CH:29]=3)[N:11]=[CH:10][C:9]=4[Cl:8])[CH2:34][CH2:35]1)(=[O:52])[CH3:51]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 66896969HCID 66896969, compound

Product 1

HCID 66896724HCID 66896724, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Chloro-12-(2-oxo-2-piperazin-1-ylethoxy)-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 trifluoroacetate (11.1 mg, 0.019 mmol) was stirred in N,N-dimethylformamide (1.0 mL) with N,N-diisopropylethylamine (17 μL, 0.096 mmol), and acetyl chloride (1.5 μL, 0.021 mmol) was added. Purification by preparative LCMS (pH 2) gave the desired compound (46%). LCMS for C26H28ClN6O3 (M+H)+: m/z=507.2.

Workup

  1. additionwas added
  2. customPurification by preparative LCMS (pH 2)

Sources & evidence

ORD record
ord-04770ad56a4b4d72968c6716c4604cef
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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