Triethylamine → HCID 23001307, compound

HRID 844268Notes

Reaction equation

HRID 844268 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[N:19]3[C:20]([CH2:23][OH:24])=[CH:21][N:22]=[C:18]3[CH2:17][CH2:16]2)=[CH:11][C:10]=1[F:25])#[N:8].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.CS(C)=O>[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[N:19]3[C:20]([CH:23]=[O:24])=[CH:21][N:22]=[C:18]3[CH2:17][CH2:16]2)=[CH:11][C:10]=1[F:25])#[N:8]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 23001316HCID 23001316, compound

Product 1

HCID 23001307HCID 23001307, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of oxalyl chloride (3.24 mL, 6.472 mmol) in methylene chloride (10 mL) at −78° C. was added DMSO (0.919 mL, 12.9 mmol). The solution was stirred for 15 minutes and a solution of the alcohol from Step I (1.11 g, 4.32 mmol) in methylene chloride (5 mL)/DMSO (1 mL) was added. The solution was stirred for an additional 15 minutes and then triethylamine (3.01 mL, 21.6 mmol) was added. The resulting solution was stirred for 5 minutes at −78° C. and 4 hours at 25° C. The reaction was poured onto sat. aq. NaHCO3 and extracted with methylene chloride (3×20 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo to provide the title product as a brown oil which was sufficiently pure for use in the next step.

Workup

  1. stirringThe solution was stirred for an additional 15 minutes
  2. stirringThe resulting solution was stirred for 5 minutes at −78° C. and 4 hours at 25° C
  3. extractionextracted with methylene chloride (3×20 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ac91c6f590eb441385ab08421416d21e
Source dataset
uspto-grants-2002_04
Patent number
US06380228B1

Reaction notes

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