2-Methoxyethyl chloroformate → HCID 71515941, compound

HRID 2277770Notes

Reaction equation

HRID 2277770 reaction equation
[C:1](Cl)(=[O:7])[O:2][CH2:3][CH2:4][O:5][CH3:6].[F:9][C:10]1[C:11]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=2[O:36][CH3:37])=[N:12][C:13]([NH:16][C:17]2[CH:22]=[C:21]([CH2:23][S:24]([CH3:27])(=[NH:26])=[O:25])[CH:20]=[C:19]([F:28])[CH:18]=2)=[N:14][CH:15]=1>N1C=CC=CC=1>[CH3:6][O:5][CH2:4][CH2:3][O:2][C:1](=[O:7])[N:26]=[S:24]([CH2:23][C:21]1[CH:22]=[C:17]([NH:16][C:13]2[N:12]=[C:11]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=3[O:36][CH3:37])[C:10]([F:9])=[CH:15][N:14]=2)[CH:18]=[C:19]([F:28])[CH:20]=1)([CH3:27])=[O:25]

Participants

4

Reactant 2

HCID 694002-Methoxyethyl chloroformateHCID 71515731HCID 71515731, compound

Product 1

HCID 71515941HCID 71515941, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Methoxyethyl carbonochloridate (18 μL; 0.15 mmol; Sigma-Aldrich Corporation) was added dropwise to a stirred solution of 5-fluoro-4-(4-fluoro-2-methoxyphenyl)-N-{3-fluoro-5-[(S-methyl-sulfonimidoyl)methyl]phenyl}pyrimidin-2-amine (Example 15; 50.0 mg; 0.12 mmol) in pyridine (1.1 mL) at 0° C. The mixture was stirred at RT for 24 hours before the batch was concentrated. Ethyl acetate and aqueous sodium chloride solution were added. The batch was extracted with ethyl acetate (2×). The combined organic phases were filtered using a Whatman filter and concentrated. The residue was purified by preparative HPLC.

Workup

  1. concentrationwas concentrated
  2. additionEthyl acetate and aqueous sodium chloride solution were added
  3. extractionThe batch was extracted with ethyl acetate (2×)
  4. filtrationThe combined organic phases were filtered
  5. filtrationfilter
  6. concentrationconcentrated
  7. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-82d0b22bf4014a9ca434e287bf04e2ae
Source dataset
uspto-grants-2015_09
Patent number
US09133171B2

Reaction notes

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