Diisopropylethylamine → HCID 49839564, compound

HRID 449888Notes

Reaction equation

HRID 449888 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]2[CH:19]=[C:18]([CH:20]([CH3:22])[CH3:21])[N:17]=[C:16](Cl)[N:15]=2)[CH:8]=1)=[O:5].C(N(C(C)C)CC)(C)C.[CH3:38][S:39]([N:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1)(=[O:41])=[O:40]>C(O)C>[Cl:28][C:24]1[CH:25]=[CH:26][CH:27]=[C:2]([Cl:1])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]2[CH:19]=[C:18]([CH:20]([CH3:22])[CH3:21])[N:17]=[C:16]([N:45]3[CH2:46][CH2:47][N:42]([S:39]([CH3:38])(=[O:41])=[O:40])[CH2:43][CH2:44]3)[N:15]=2)[CH:8]=1)=[O:5]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 7091611-(Methylsulfonyl)piperazineHCID 86648952HCID 86648952, compound

Product 1

HCID 49839564HCID 49839564, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

To a microwave tube with a solution of 2,6-dichloro-N-(2-(2-chloro-6-isopropylpyrimidin-4-ylamino)pyridin-4-yl)benzamide (0.050 g, 0.11 mmol) in ethanol (2 mL) was added diisopropylethylamine (1.5 mL) and 1-(methylsulfonyl)piperazine (0.18 g, 1.1 mmol). The resulting mixture was heated to 140° C. under microwave irradiation for 2 hours. The mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to give the desired product (30 mg, 46% yield). 1H NMR ((500 MHz, DMSO-d6): δ 11.05 (s, 1H), 9.77 (s, 1H), 8.77 (s, 1H), 8.16 (d, J=5.5 Hz, 1H), 7.63 (s, 1H), 7.61 (s, 1H), 7.54 (m, 1H), 6.87 (m, 1H), 6.48 (s, 1H), 3.95-3.91 (m, 4H), 3.17-3.14 (m, 4H), 2.85 (s, 3H), 2.67 (m, 1H), 1.17 (d, J=7.0 Hz, 6H). LCMS (ESI) m/z: 564.0 [M+H+].

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min)

Sources & evidence

ORD record
ord-824446baa6e64adea3954a809aa1520b
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Reaction notes

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