Dichloromethane → HCID 23139542, compound

HRID 407494

Reaction equation

HRID 407494 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:7]=1[C:13]1[N:14]([CH3:18])[N:15]=[CH:16][CH:17]=1.C(Cl)Cl.Cl[C:24](OC1C=CC([N+]([O-])=O)=CC=1)=[O:25].[NH2:36][C:37]1[CH:47]=[CH:46][C:40]2[O:41][C:42]([F:45])([F:44])[O:43][C:39]=2[CH:38]=1>>[F:44][C:42]1([F:45])[O:41][C:40]2[CH:46]=[CH:47][C:37]([NH:36][C:24]([NH:12][C:9]3[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][N:2]([CH3:19])[CH3:1])=[C:7]([C:13]4[N:14]([CH3:18])[N:15]=[CH:16][CH:17]=4)[CH:8]=3)=[O:25])=[CH:38][C:39]=2[O:43]1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 821294-Nitrophenyl chloroformateHCID 27368935-Amino-2,2-difluoro-1,3-benzodioxoleHCID 23139532HCID 23139532, compound

Product 1

HCID 23139542HCID 23139542, compoundYield 14%

Procedure

To a solution of 4-(2-dimethylamino-ethoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenylamine (26.0 mg, 0.1 mmol) in methylene chloride (1 mL) pyridine (24.3 μL, 0.3 mmol) and 4-nitrophenyl chloroformate (20.2 mg, 0.1 mmol) were added and the mixture was stirred at room temperature for 1 hour. 5-Amino-2,2-difluoro-1,3-benzodioxole (11.6 μL, 0.1 mmol) was added, the reaction mixture stirred at room temperature for 48 hours and concentrated to give an oily residue that was subjected to a purification by flash chromatography (SiO2, CH2Cl2/MeOH gradient elution) to afford Compound 144 as an off-white solid in 14.0% yield. LCMS m/z (%)=460 (M+H, 100). 1H NMR (400 MHz, DMSO-d6) δ: 10.30 (s, 1H), 7.64 (d, J=8.96 Hz, 1H), 7.53 (s, 1H), 7.42 (s, 1H), 7.40-7.34 (m, 4H), 7.13 (d, J=8.92 Hz, 1H), 6.22 (s, 1H), 4.10 (t, J=5.56 Hz, 2H), 3.65 (s, 3H), 3.63 (s, 2H), 2.76-2.65 (m, 2H), 2.22 (s, 6H).

Workup

  1. stirringthe reaction mixture stirred at room temperature for 48 hours
  2. concentrationconcentrated
  3. customto give an oily residue that
  4. customwas subjected to a purification by flash chromatography (SiO2, CH2Cl2/MeOH gradient elution)

Sources & evidence

ORD record
ord-f0a0e4bf8a024e1694aa2b0095df4ecb
Source dataset
uspto-grants-2014_06
Patent number
US08754238B2

Linked notes

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