Monochloramine → HCID 59856755, compound

HRID 2377913Notes

Reaction equation

HRID 2377913 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[C:19]([N+:20]([O-])=O)=[C:18]([NH:23][C:24]3[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][C:25]=3[F:34])[N:17]=[CH:16][N:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].NCl>C1COCC1.O.[Zn]>[CH:1]([O:4][C:5]([N:7]1[CH2:8][CH2:9][CH:10]([O:13][C:14]2[C:19]([NH2:20])=[C:18]([NH:23][C:24]3[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][C:25]=3[F:34])[N:17]=[CH:16][N:15]=2)[CH2:11][CH2:12]1)=[O:6])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 25423MonochloramineHCID 67203683HCID 67203683, compound

Product 1

HCID 59856755HCID 59856755, compoundYield 71.3%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Mixture of 4-[6-(2-fluoro-4-methanesulfonyl-phenylamino)-5-nitro-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid isopropyl ester (197 mg, 0.3 mmole), Zn Dust (2.4 mmole, 8 eq) and 1 mL of Sat NH2Cl solution in 2 mL THF and 2 mL H2O was stirred at room temperature for 25 minutes. Zn Dust was filtered off by celite and washed with ethyl acetate. Crude was purified by column chromatography (Hexane/Ethyl Acetate=½, Rf=0.44) to give compound A120 as a yellow oil (100 mg, 71%). 1H NMR (DMSO-d6, 400 MHz) δ 1.19 (d, 6H), 1.62-1.68 (m, 2H), 1.88-1.93 (m, 2H), 3.23 (s, 3H), 3.33-3.39 (m, 2H), 3.64-3.70 (m, 2H), 4.77 (sep, 1H), 5.28-5.29 (m, 1H), 7.68 (d, 1H), 7.77 (d, 1H), 7.88 (s, 1H), 8.06 (t, 1H), 8.41 (sb, NH). Exact mass calculated for C20H26FN5O5S 467.2, found 468.5 (MH+).

Workup

  1. filtrationZn Dust was filtered off by celite
  2. washwashed with ethyl acetate
  3. customCrude was purified by column chromatography (Hexane/Ethyl Acetate=½, Rf=0.44)

Sources & evidence

ORD record
ord-ea6751fde964468095d72c06385e39a8
Source dataset
uspto-grants-2008_12
Patent number
US07470699B2

Reaction notes

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