Triethylamine → HCID 87304736, compound

HRID 1853319Notes

Reaction equation

HRID 1853319 reaction equation
[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][CH2:18][CH2:19][CH2:20][OH:21])[CH:15]=2)[O:10][C:9]([C:22]2[N:27]=[CH:26][N:25]3[CH:28]=[CH:29][CH:30]=[C:24]3[CH:23]=2)=[CH:8]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40].[Cl-].[NH4+]>ClCCl>[C:1]([O:5]/[N:6]=[C:7]1\[CH:8]=[C:9]([C:22]2[N:27]=[CH:26][N:25]3[CH:28]=[CH:29][CH:30]=[C:24]3[CH:23]=2)[O:10][C:11]2[C:16]\1=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][O:21][S:39]([CH3:38])(=[O:41])=[O:40])=[CH:13][CH:12]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 86673083HCID 86673083, compound

Product 1

HCID 87304736HCID 87304736, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A ice-cooled solution of 6-(4-Hydroxy-butyl)-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one O-tert-butyl-oxime (115 mg, 0.28 mmol) (example 102B) in dichloromethane (5 ml) was treated with triethylamine (100 μl, 0.7 mmol) and dropwise with methanesulfonyl chloride (26 μl, 0.34 mmol). The mixture was stirred at room temperature for 3 hours and treated with a saturated solution of ammonium chloride, extracted with dichloromethane, washed with brine, dried over sodium sulfate and concentrated to dryness. The crude mesylate was used for the next step without further purification.

Workup

  1. extractionextracted with dichloromethane
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness
  5. customThe crude mesylate was used for the next step without further purification

Sources & evidence

ORD record
ord-c3f8bde1ec574ab2837d7a0e721a592c
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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