Toluene → 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

HRID 541768Notes

Reaction equation

HRID 541768 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:5]=[N:6][C:7]2[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[C:13]([CH:26]=3)[CH2:14][CH2:15][C:16]3[CH:24]=[C:20]([NH:21][C:22]=1[N:23]=2)[CH:19]=[CH:18][C:17]=3[NH2:25].C(N(CC)C(C)C)(C)C.[C:36](Cl)(Cl)=[O:37].C1(C)C=CC=CC=1.[NH2:47][CH2:48][CH2:49][NH:50][C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52]>C(Cl)Cl>[Cl:3][C:4]1[CH:5]=[N:6][C:7]2[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[C:13]([CH:26]=3)[CH2:14][CH2:15][C:16]3[CH:24]=[C:20]([NH:21][C:22]=1[N:23]=2)[CH:19]=[CH:18][C:17]=3[NH:25][C:36]([NH:47][CH2:48][CH2:49][NH:50][C:51](=[O:52])[O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:37]

Participants

7

Reactant 5

HCID 1140TolueneHCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 187201N-BOC-ethylenediamineHCID 668960506-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-amine Dihydrochloride

Product 1

HCID 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}carbamateYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 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-amine dihydrochloride (314 mg, 0.764 mmol) in DCM (3.4 mL) were added N,N-diisopropylethylamine (0.53 mL, 3.1 mmol) and 20% phosgene in toluene (0.53 mL, 0.99 mmol). After stirring for 2 hours, N-(2-aminoethyl)(tert-butoxy)carboxamide (0.182 mL, 1.15 mmol) was added to reaction flask and stirred overnight. The resulting precipitate was filtered and washed with DCM to yield the desired product (326 mg, 81%). LCMS calculated for C26H31ClN7O3(M+H)+: m/z=524.3.

Workup

  1. stirringstirred overnight
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with DCM

Sources & evidence

ORD record
ord-791d09a0713b46089e2a966e49dd3e41
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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