2-Chloroethyl chloroformate → HCID 86716492, compound

HRID 1747718Notes

Reaction equation

HRID 1747718 reaction equation
Cl.Cl.Cl.[F:4][C:5]1[CH:29]=[CH:28][CH:27]=[CH:26][C:6]=1[CH2:7][C:8]1[N:12]2[N:13]=[CH:14][CH:15]=[CH:16][C:11]2=[C:10]([C:17]2[N:22]=[C:21]([NH2:23])[C:20]([NH2:24])=[C:19]([NH2:25])[N:18]=2)[N:9]=1.Cl[C:31]([O:33][CH2:34][CH2:35][Cl:36])=[O:32]>N1C=CC=CC=1.ClCCl>[NH2:25][C:19]1[C:20]([NH:24][C:31](=[O:32])[O:33][CH2:34][CH2:35][Cl:36])=[C:21]([NH2:23])[N:22]=[C:17]([C:10]2[N:9]=[C:8]([CH2:7][C:6]3[CH:26]=[CH:27][CH:28]=[CH:29][C:5]=3[F:4])[N:12]3[C:11]=2[CH:16]=[CH:15][CH:14]=[N:13]3)[N:18]=1

Participants

5

Reactant 2

HCID 123052-Chloroethyl chloroformate2×HCID 86716493HCID 86716493, compound

Product 1

HCID 86716492HCID 86716492, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

247 mg (0.623 mmol) of the compound prepared in Example 9A were initially charged in pyridine (2.5 ml) and dichloromethane (2.5 ml), 64 μl (0.623 mmol) of 2-chloroethyl chloroformate were added at 0° C. and the mixture was stirred at 0° C. for 10 min. After 16 hours of stirring at 20° C., another 64 μl (0.623 mmol) of 2-chloroethyl chloroformate were added, and the mixture was stirred at 20° C. for 16 hours. The reaction mixture was then poured onto ice-water and extracted twice with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated. The residue (314 mg) was used for the next step without further purification.

Workup

  1. stirringAfter 16 hours of stirring at 20° C.
  2. stirringthe mixture was stirred at 20° C. for 16 hours
  3. additionThe reaction mixture was then poured onto ice-water
  4. extractionextracted twice with dichloromethane
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue (314 mg) was used for the next step without further purification

Sources & evidence

ORD record
ord-8b6fbd63ff384745af31516fc188a10f
Source dataset
uspto-grants-2015_10
Patent number
US09150580B2

Reaction notes

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