Diisopropylethylamine → HCID 11547279, compound

HRID 643488Notes

Reaction equation

HRID 643488 reaction equation
[CH3:1][C@@:2]1([CH2:9][S:10](Cl)(=[O:12])=[O:11])[C:6](=[O:7])[NH:5][C:4](=[O:8])[NH:3]1.[F:14][C:15]([F:33])([F:32])[C:16]1[N:21]=[CH:20][C:19]([C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[CH2:28][NH:27][CH2:26][CH2:25]3)=[CH:18][N:17]=1.CCN(C(C)C)C(C)C>C1COCC1.O.[Cl-].[Na+].O>[CH3:1][C@:2]1([CH2:9][S:10]([N:27]2[CH2:26][CH2:25][C:24]3[C:29](=[CH:30][CH:31]=[C:22]([C:19]4[CH:20]=[N:21][C:16]([C:15]([F:33])([F:14])[F:32])=[N:17][CH:18]=4)[CH:23]=3)[CH2:28]2)(=[O:12])=[O:11])[NH:3][C:4](=[O:8])[NH:5][C:6]1=[O:7]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 16738713(4S)-(4-methyl-2,5-dioxoimidazolidin-4-yl)methanesulphonyl chlorideHCID 686028176-[2-(Trifluoromethyl)pyrimidin-5-yl]-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 11547279HCID 11547279, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 23713072Sodium chloride dihydrateSolvent

Procedure

[(4S)-4-Methyl-2,5-dioxoimidazolidin-4-yl]methanesulfonyl chloride (0.0295 g, 0.13 mmol) in dry THF (0.60 mL) was added dropwise to a stirred solution of 6-[2-(trifluoromethyl)pyrimidin-5-yl]-1,2,3,4-tetrahydroisoquinoline (0.039 g, 0.14 mmol), DIPEA (0.034 mL, 0.20 mmol) and dry THF (0.60 mL) at ice-bath temperature. After the addition was complete the solution was stirred at RT for 2 h and then taken up in water-brine and extracted twice with EtOAc. The combined organic phases were washed with brine, dried, filtered and concentrated to give a crude product. Purification by preparative HPLC afforded 0.050 g (76%) of the title compound as a white solid.

Workup

  1. additionAfter the addition
  2. extractionextracted twice with EtOAc
  3. washThe combined organic phases were washed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude product
  8. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-39d52fe6d35a4c5da1d36cd3ba9fb31c
Source dataset
uspto-grants-2010_04
Patent number
US07700604B2

Reaction notes

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