Acetone → HCID 67441539, compound

HRID 1400838Notes

Reaction equation

HRID 1400838 reaction equation
[NH2:1][C:2]1[CH:30]=[CH:29][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[CH:13]=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([C:22]([N:24]5[CH2:28][CH2:27][CH2:26][CH2:25]5)=[O:23])=[CH:18][CH:17]=4)[S:15][C:8]=23)=[C:4]([F:31])[CH:3]=1.ClC(Cl)(O[C:36](=[O:42])OC(Cl)(Cl)Cl)Cl.[Cl-].[CH3:45][S:46]([C:49]1[CH:50]=[C:51]([NH3+:55])[CH:52]=[CH:53][CH:54]=1)(=[O:48])=[O:47].CC(C)=O>C1COCC1>[F:31][C:4]1[CH:3]=[C:2]([NH:1][C:36]([NH:55][C:51]2[CH:52]=[CH:53][CH:54]=[C:49]([S:46]([CH3:45])(=[O:48])=[O:47])[CH:50]=2)=[O:42])[CH:30]=[CH:29][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]2[CH:13]=[C:14]([C:16]3[CH:17]=[CH:18][C:19]([C:22]([N:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)=[O:23])=[CH:20][CH:21]=3)[S:15][C:8]=12

Participants

6

Reactant 4

HCID 180AcetoneHCID 94429TriphosgeneHCID 2736957HCID 2736957, compoundHCID 58474497HCID 58474497, compound

Product 1

HCID 67441539HCID 67441539, compoundYield 11.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 126 (150 mg, 0.346 mmol) in THF (6 mL) was added TEA (175 mg, 1.730 mmol) and triphosgene (103 mg, 0.346 mmol) in THF (1 mL) and the mixture was stirred for 30 minutes. 3-(Methylsulfonyl)benzenaminium chloride (144 mg, 0.692 mmol) was added and the mixture was stirred at RT overnight. The mixture was then concentrated and the resultant solid was triturated with acetone, DCM and MeOH, followed by recrystallization from hot DMF. An additional trituration with acetone afforded 130 (25 mg, 11% yield) as a grey powder. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.32 (s, 1H), 9.24 (s, 1H), 8.52 (d, J=5.48 Hz, 1H), 8.16 (s, 1H), 8.13 (s, 1H), 7.94 (d, J=8.41 Hz, 2H), 7.75 (m, 1H), 7.66-7.62 (m, 3H), 7.56-7.53 (m, 2H), 7.45 (m, 1H), 7.31 (m, 1H), 6.64 (d, J=5.48 Hz, 1H), 3.48-3.37 (m, 4H), 3.19 (s, 3H), 1.86-1.81 (m, 4H). MS (m/z)=631.437 (M+H).

Workup

  1. stirringthe mixture was stirred at RT overnight
  2. concentrationThe mixture was then concentrated
  3. customthe resultant solid was triturated with acetone, DCM and MeOH
  4. customfollowed by recrystallization from hot DMF

Sources & evidence

ORD record
ord-e2a163d2ae8248ac8c098155d2a8ec9a
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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