Water → HCID 59004525, compound

HRID 1255133Notes

Reaction equation

HRID 1255133 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=[C:10]([CH2:12]O)[N:11]=1)=[O:5].O=S(Cl)[Cl:31].CCN(CC)CC.O>C(Cl)Cl>[Cl:31][CH2:12][C:10]1[N:11]=[C:7]([NH:6][C:4](=[O:5])[C:3]2[C:2]([F:1])=[CH:27][CH:26]=[CH:25][C:24]=2[F:28])[S:8][C:9]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 24765213HCID 24765213, compound

Product 1

HCID 59004525HCID 59004525, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a solution of Compound 39 (123 mg, 0.3 mmol) in 5 mL of CH2Cl2 was added SOCl2 (0.4 mmol) and NEt3 (0.5 mmol) at room temperature. The solution was stirred at room temperature for 2 hours. The solution was treated with 10 mL of water and extracted with CH2Cl2. The combined extracts were washed with water, dried (Na2SO4), filtered and concentrated. The residue was purified on silica (eluted with 5-50% ethyl acetate in hexane) to give Compound 70 (114 mg, 88%) as a white solid.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe combined extracts were washed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on silica (eluted with 5-50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-8b4ede9007d94a7fa2365c8d83b5dab2
Source dataset
uspto-grants-2013_06
Patent number
US08455658B2

Reaction notes

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