Iodoethane → HCID 21886169, compound

HRID 723112Notes

Reaction equation

HRID 723112 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:17]1[CH:18]=[C:19]([S:23]([C:26]2[CH:27]=[C:28]([C:33]([NH2:35])=[NH:34])[S:29][C:30]=2[S:31][CH3:32])(=[O:25])=[O:24])[CH:20]=[CH:21][CH:22]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:43][CH3:44]>CC(C)=O>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:43]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:17]1[CH:18]=[C:19]([S:23]([C:26]2[CH:27]=[C:28]([C:33]([NH2:35])=[NH:34])[S:29][C:30]=2[S:31][CH3:32])(=[O:25])=[O:24])[CH:20]=[CH:21][CH:22]=1)[CH3:44]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 21886615HCID 21886615, compound

Product 1

HCID 21886169HCID 21886169, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture containing ({4-[3-(1H-benzoimidazol-2-yl)-benzenesulfonyl]-5-methylsulfanyl-thiophen-2-yl}-imino-methyl)-carbamic acid tert-butyl ester (prepared in Example 144) (25 mg, 0.05 mmol), K2CO3 (13 mg, 0.10 mmol), and iodoethane (12 mg, 0.08 mmol) in 0.5 mL acetone was heated to 60° C. for 2 hrs. The mixture was filtered then concentrated, and the residue dissolved in 0.5 ml of 50% TFA/DCM and stirred at 25° C. for 30 mins. The solvent was evaporated and the crude product purified by RP-HPLC, eluting with a linear gradient of 10% CH3CN in 0.1% TFA/H2O to 50% CH3CN over 30 mins, to give 26 mg (93%) of the title compound as yellow solid: 1H NMR (400 MHz, CD3OD) δ 8.58 (m, 1H), 8.44 (m, 1H), 8.41 (s, 1H), 8.20 (m, 1H), 8.02 (m, 2H), 7.90 (m, 1H), 7.71 (m, 2H), 4.55 (q, 2H), 2.75 (s, 3H), 1.59 (t, 3H). Mass spectrum (ESI, m/z) calcd. for C21H20N4O2S3 456.1, found 457.1 (M+H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthen concentrated
  3. dissolutionthe residue dissolved in 0.5 ml of 50% TFA/DCM
  4. customThe solvent was evaporated
  5. customthe crude product purified by RP-HPLC
  6. washeluting with a linear gradient of 10% CH3CN in 0.1% TFA/H2O to 50% CH3CN over 30 mins

Sources & evidence

ORD record
ord-76486667b9734f6687964fed6dbfd554
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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