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Hydrochloric Acid → N-(2-Aminoethyl)-N'-[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]urea Dihydrochloride

HRID 541769
Notes
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Reaction equation

HRID 541769 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][CH:10]=[C:11]([CH:37]=3)[CH2:12][CH2:13][C:14]3[CH:22]=[C:18]([NH:19][C:20]=1[N:21]=2)[CH:17]=[CH:16][C:15]=3[NH:23][C:24]([NH:26][CH2:27][CH2:28][NH:29]C(=O)OC(C)(C)C)=[O:25].[ClH:38].O1CCOCC1>C(Cl)Cl.CCOCC>[ClH:1].[ClH:38].[NH2:29][CH2:28][CH2:27][NH:26][C:24]([NH:23][C:15]1[CH:16]=[CH:17][C:18]2[NH:19][C:20]3[N:21]=[C:5]([NH:6][C:7]4[CH:8]=[CH:9][CH:10]=[C:11]([CH:37]=4)[CH2:12][CH2:13][C:14]=1[CH:22]=2)[N:4]=[CH:3][C:2]=3[Cl:1])=[O:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 57962053Tert-butyl {2-[({[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]amino}carbonyl)amino]ethyl}carbamate

Product 1

HCID 66897172N-(2-Aminoethyl)-N'-[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]urea DihydrochlorideYield 79%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl {2-[({[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]amino}carbonyl)amino]ethyl}carbamate (326 mg, 0.622 mmol) in DCM (12 mL) was added 4.0 M of hydrogen chloride in 1,4-dioxane (0.544 mL, 2.18 mmol). After stirring overnight, the reaction solution was diluted with ether. The resulting precipitate was filtered and dried under vacuum to give the desired product (245 mg, 79%). LCMS calculated for C21H23ClN7O (M+H)+: m/z=424.2.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. customdried under vacuum

Sources & evidence

ORD record
ord-bd7b992b5f084d47adafa8f05af4de94
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08871753B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes