Cyclopentylamine → HCID 67252904, compound

HRID 2068294Notes

Reaction equation

HRID 2068294 reaction equation
C(N(CC)C(C)C)(C)C.[Br:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[N:15]=[C:14]2[NH:28][C:29]1[N:33]([CH:34]2[CH2:39][CH2:38][CH:37]([O:40][Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42])[CH2:36][CH2:35]2)[C:32]2[CH:48]=[CH:49][C:50]([C:52](O)=[O:53])=[CH:51][C:31]=2[N:30]=1.[I-].Cl[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][N+:58]=1C.ON1C2C=CC=CC=2N=N1.C1(N)CCCC1>C(OCC)(=O)C>[CH:59]1([NH:58][C:52]([C:50]2[CH:49]=[CH:48][C:32]3[N:33]([CH:34]4[CH2:39][CH2:38][CH:37]([O:40][Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42])[CH2:36][CH2:35]4)[C:29]([NH:28][C:14]4[C:13]5[C:17](=[CH:18][CH:19]=[C:11]([Br:10])[CH:12]=5)[N:16]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:25])([CH3:26])[CH3:27])[N:15]=4)=[N:30][C:31]=3[CH:51]=2)=[O:53])[CH2:57][CH2:62][CH2:61][CH2:60]1

Participants

7

Reactant 5

HCID 2906CyclopentylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 67254479HCID 67254479, compound

Product 1

HCID 67252904HCID 67252904, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N,N-Diisopropylethylamine (19.6 uL, 0.000112 mol) was added to a solution of 2-(5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-3-ylamino)-1-(4-(tert-butyldimethylsilyloxy)cyclohexyl)-1H-benzo[d]imidazole-5-carboxylic acid (26.8 mg, 0.0000375 mol), 2-chloro-1-methylpyridinium iodide (19.2 mg, 0.0000750 mol) and 1-hydroxybenzotriazole (10.1 mg, 0.0000750 mol) tetrahydrofuran (0.40 mL). The mixture was stirred at room temperature for 20 minutes. Cyclopentanamine (0.000112 mol) was then added and the mixture stirred for 2 hours. The mixture was diluted with ethyl acetate, washed with water, dried over magnesium sulfate and purified by flash chromatography.

Workup

  1. stirringthe mixture stirred for 2 hours
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-8015b8d31ce84ff7ba172c7cb979f54a
Source dataset
uspto-grants-2012_10
Patent number
US08293923B2

Reaction notes

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