Diisopropylethylamine → HCID 67478923, compound

HRID 1092217Notes

Reaction equation

HRID 1092217 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[NH:11][N:10]=2)[C:5]([N+:17]([O-:19])=[O:18])=[CH:4][N:3]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([C@@H:27]([NH2:29])[CH3:28])=[CH:23][CH:22]=1.CCN(C(C)C)C(C)C>CCCCO>[CH:14]1([C:12]2[NH:11][N:10]=[C:9]([NH:8][C:6]3[C:5]([N+:17]([O-:19])=[O:18])=[CH:4][N:3]=[C:2]([NH:29][C@H:27]([C:24]4[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=4)[CH3:28])[N:7]=3)[CH:13]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2779063(S)-1-(4-Fluorophenyl)-ethylamineHCID 866217662-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-nitro-pyrimidin-4-amine

Product 1

HCID 67478923HCID 67478923, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-nitropyrimidin-4-amine (Method 76; 1.0 g, 3.6 mmol), (S)-1-(4-fluorophenyl)ethanamine (0.5 g, 3.6 mmol), and DIEA (0.6 g, 4.6 mmol) in n-BuOH (15 ml) was stirred at 25° C. for 1 hour and then concentrated. The resulting oil was purified by column chromatography (DCM:MeOH=50:1) to give the title compound (0.8 g, 60%). MS: Calcd.: 383; Found: [M+H]+ 384.

Workup

  1. concentrationconcentrated
  2. customThe resulting oil was purified by column chromatography (DCM:MeOH=50:1)

Sources & evidence

ORD record
ord-6f6d35e5efd84aab8f1c3484336d89b6
Source dataset
uspto-grants-2012_03
Patent number
US08129403B2

Reaction notes

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