Dichloromethane → HCID 69015898, compound

HRID 541576Notes

Reaction equation

HRID 541576 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(Cl)Cl.C(N(CC)CC)C.[N:51]([C:54]1[CH:61]=[CH:60][C:57]([C:58]#[N:59])=[CH:56][CH:55]=1)=[C:52]=[O:53]>CN(C)C=O>[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]([N:33]1[CH2:38][CH2:37][N:36]([C:52]([NH:51][C:54]2[CH:61]=[CH:60][C:57]([C:58]#[N:59])=[CH:56][CH:55]=2)=[O:53])[CH2:35][CH2:34]1)=[O:39]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 1703804-Cyanophenyl isocyanateHCID 66896969HCID 66896969, compound

Product 1

HCID 69015898HCID 69015898, compoundYield 8%

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 (10.0 mg, 0.017 mmol) was stirred in N,N-dimethylformamide (0.5 mL) and methylene chloride (0.5 mL) with triethylamine (12.0 μL, 0.086 mmol), and 4-isocyanatobenzonitrile (2.7 mg, 0.019 mmol) was added. Purification by preparative LCMS (pH 2) gave the desired compound (8%). LCMS for C32H30ClN8O3 (M+H)+: m/z=609.2.

Workup

  1. customPurification by preparative LCMS (pH 2)

Sources & evidence

ORD record
ord-3cd29970d1344f238b79afba595cbc19
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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