Pyridine → HCID 57962571, compound

HRID 541790Notes

Reaction equation

HRID 541790 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].N1C=CC=CC=1.[C:33](Cl)(Cl)=[O:34].C1(C)C=CC=CC=1.[NH:44]1[CH2:48][CH2:47][C@@H:46]([NH:49][C:50](=[O:56])[O:51][C:52]([CH3:55])([CH3:54])[CH3:53])[CH2:45]1>C(Cl)Cl.CO>[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:33]([N:44]1[CH2:48][CH2:47][C@@H:46]([NH:49][C:50](=[O:56])[O:51][C:52]([CH3:53])([CH3:55])[CH3:54])[CH2:45]1)=[O:34]

Participants

8

Reactant 5

HCID 1049Pyridine2×HCID 1140TolueneHCID 6371PhosgeneHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 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 57962571HCID 57962571, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture 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 (30 mg, 0.07 mmol) and pyridine (18.9 μL, 0.234 mmol) in methylene chloride (0.4 mL) was added 20% phosgene in toluene (1:4, phosgene:toluene, 50.2 μL, 0.0950 mmol). The resulting mixture was stirred for 1 hour before adding tert-butyl (3R)-pyrrolidin-3-ylcarbamate (14.3 mg, 0.0767 mmol) and pyridine (13.0 μL, 0.161 mmol). The mixture was allowed to stir overnight. It was diluted with methanol and purified by preparative LCMS (pH 10) to give the desired product. LCMS calculated for C28H33ClN7O3 (M+H)+: m/z=550.2.

Workup

  1. stirringto stir overnight
  2. custompurified by preparative LCMS (pH 10)

Sources & evidence

ORD record
ord-1f03528371154e86a0ccded24a1dc812
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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