Sodium Iodide → HCID 88296093, compound

HRID 1603239Notes

Reaction equation

HRID 1603239 reaction equation
O[CH2:2][C:3]1[C:16]2[O:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([OH:17])[CH:13]=3)[C:8]3([C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19](=[O:26])[O:18]3)[C:7]=2[CH:6]=[CH:5][C:4]=1[OH:27].[F:28][C:29]([F:52])([F:51])[C:30]([NH:32][C@@H:33]([CH3:50])[CH2:34][C:35]1[CH:40]=[CH:39][C:38]([S:41]([N:44]2[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]2)(=[O:43])=[O:42])=[CH:37][CH:36]=1)=[O:31].[I-].[Na+].N1C(C)=CC=CC=1C>CN(C)C=O>[OH:27][C:4]1[CH:5]=[CH:6][C:7]2[C:8]3([C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19](=[O:26])[O:18]3)[C:9]3[C:14]([O:15][C:16]=2[C:3]=1[CH2:2][N:47]1[CH2:48][CH2:49][N:44]([S:41]([C:38]2[CH:37]=[CH:36][C:35]([CH2:34][C@@H:33]([NH:32][C:30](=[O:31])[C:29]([F:52])([F:51])[F:28])[CH3:50])=[CH:40][CH:39]=2)(=[O:42])=[O:43])[CH2:45][CH2:46]1)=[CH:13][C:12]([OH:17])=[CH:11][CH:10]=3

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 79372,6-LutidineHCID 19609083HCID 19609083, compoundHCID 53991055HCID 53991055, compound

Product 1

HCID 88296093HCID 88296093, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 61 mg (0.160 mmol) of rac-4'-(hydroxymethyl)-3',6'-dihydroxyspiro[isobenzofuran-1(3H), 9'-[9H]xanthen]-3-one (2), 125 mg (0.33 mmole) of (S)-2,2,2-trifluoro-N-[1-methyl-2-[4-(1-piperazinylsulfonyl)phenyl]ethyl]acetamide (17), 150 mg (1.0 mmol) of sodium iodide and 600 μL (5.15 mmol) of 2,6 lutidine in 4.5 mL of anhydrous dimethylformamide was heated at 120° C. for 2 hours. The reaction mixture was concentrated and 20 mL of a 1:1 mixture of methanol:THF was added. Inorganic salt was filtered off and the filtrate was concentrated. The residue was purified by thin layer chromatography using 50% chloroform in ethyl acetate to yield 41 mg of (S)-N-[2-[4-[[4-[(3',6'-dihydroxy-3-oxospiro[isobenzo-furan-1(3H),9'-[9H]xanthen]-4'-yl)methyl]-1-piperazinyl]-sulfonyl]phenyl]-1-methylethyl]-2,2,2-trifluoroacetamide (1:1 epimers) (18) (0.056 mmol, 35%) as an orange red powder. NMR, IR and MS data confirmed the compound identity.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition20 mL of a 1:1 mixture of methanol
  3. additionTHF was added
  4. filtrationInorganic salt was filtered off
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-d394811cd3cb49e69dbebb21d82374c1
Source dataset
uspto-grants-1999_11
Patent number
US05986094

Reaction notes

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