Diisopropylethylamine → HCID 67042162, compound

HRID 2047632Notes

Reaction equation

HRID 2047632 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:9][C:10]([CH3:19])([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:5]([N+:25]([O-:27])=[O:26])=[CH:4][N:3]=1.N[C:29]1[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][C:30]=1[O:39][CH3:40].[CH3:41]CN(C(C)C)C(C)C>CC(C)CC(O)C>[C:14]([O:13][C:11](=[O:12])[C:10]([CH3:19])([CH3:18])[CH2:9][N:8]([CH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)[C:6]1[C:5]([N+:25]([O-:27])=[O:26])=[CH:4][N:3]=[C:2]([NH:7][C:29]2[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][C:30]=2[O:39][CH3:40])[CH:41]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 602411Methyl 4-amino-3-methoxybenzoateHCID 53375440HCID 53375440, compound

Product 1

HCID 67042162HCID 67042162, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 79104-Methyl-2-PentanolSolvent

Procedure

tert-butyl 3-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]-2,2-dimethyl-propanoate (1.5 g, 3.760 mmol), methyl 4-amino-3-methoxy-benzoate (817.5 mg, 4.512 mmol) and DIPEA (728.9 mg, 982.3 μL, 5.640 mmol) in 4-methylpentan-2-ol were treated under microwave at 140 C for 2 hours. The mixture was concentrated and purification by flash chromatography, eluting with 5% ethylacetate/petether to remove impurities followed by 10% ethylacetate/pet ether to elute product, gave methyl 4-(4-((3-tert-butoxy-2,2-dimethyl-3-oxopropyl) (cyclopentyl)amino)-5-nitropyridin-2-ylamino)-3-methoxybenzoate as a yellow oil (1.25 g, 61%). NMR CDCl3 1.18 (6H, s), 1.46 (9H, s), 1.52-1.58 (2H, m), 1.63-1.70 (2H, m), 1.72-1.80 (2H, m), 1.92-1.98 (2H, m), 3.62-3.68 (1H, m), 3.85-4.0 (8H, m), 7.55 (1H, s), 7.72-7.75 (1H, m), 8.12 (1H, brs), 8.5 (1H, d), 8.97 (1H, s); MS (ES+) 544.1 (ES−) 542.1

Workup

  1. concentrationThe mixture was concentrated
  2. custompurification by flash chromatography
  3. washeluting with 5% ethylacetate/petether
  4. customto remove impurities
  5. washto elute product

Sources & evidence

ORD record
ord-262921e1e45f4d6e9dee2b4a7cd62fd5
Source dataset
uspto-grants-2013_11
Patent number
US08592577B2

Reaction notes

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