Diisopropylethylamine → [4-({5-Nitro-2-[(quinolin-5-ylmethyl)-amino]-pyrimidin-4-ylamino}-methyl)-cyclohexyl]-carbamic acid tert-butyl ester

HRID 1819453Notes

Reaction equation

HRID 1819453 reaction equation
[N:1]1[C:10]2[C:5](=[C:6](NC)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH:13]([N:16](C(C)C)CC)(C)C.[C:22]([O:26][C:27](=[O:47])[NH:28][CH:29]1[CH2:34][CH2:33][CH:32]([CH2:35][NH:36][C:37]2[C:42]([N+:43]([O-:45])=[O:44])=[CH:41][N:40]=[C:39](Cl)[N:38]=2)[CH2:31][CH2:30]1)([CH3:25])([CH3:24])[CH3:23]>CN(C=O)C.C(#N)C.C(OCC)(=O)C>[C:22]([O:26][C:27](=[O:47])[NH:28][CH:29]1[CH2:34][CH2:33][CH:32]([CH2:35][NH:36][C:37]2[C:42]([N+:43]([O-:45])=[O:44])=[CH:41][N:40]=[C:39]([NH:16][CH2:13][C:6]3[CH:7]=[CH:8][CH:9]=[C:10]4[C:5]=3[CH:4]=[CH:3][CH:2]=[N:1]4)[N:38]=2)[CH2:31][CH2:30]1)([CH3:25])([CH3:24])[CH3:23]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 348010N-methylquinolin-5-amineHCID 57885529(4-[(2-Chloro-5-nitro-pyrimidin-4-ylamino)-methyl]cyclohexyl)-carbamic acid tert-butyl ester

Product 1

HCID 57885717[4-({5-Nitro-2-[(quinolin-5-ylmethyl)-amino]-pyrimidin-4-ylamino}-methyl)-cyclohexyl]-carbamic acid tert-butyl esterYield 100%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of quinolin-5-yl-methylamine 100 mg, 0.39 mmol) and diisopropylethylamine (140 μL, 0.78 mmol) in a mixture of DMF (2 mL) and acetonitrile (2 mL) was added {4-[(2-chloro-5-nitro-pyrimidin-4-ylamino)-methyl]-cyclohexyl}-carbamic acid tert-butyl ester (150 mg, 0.39 mmol). The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with ethyl acetate and washed with water (×2). The combined organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 95:5 CH2Cl2:MeOH as an eluent to afford 197 mg of [4-({5-nitro-2-[(quinolin-5-ylmethyl)-amino]-pyrimidin-4-ylamino}-methyl)-cyclohexyl]-carbamic acid tert-butyl ester as a light yellow solid (100%).

Workup

  1. washwashed with water (×2)
  2. dry with materialThe combined organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-2e2471cf9ea442e29a87d39e27ff0d45
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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