Phenol → HCID 11049045, compound

HRID 1432954Notes

Reaction equation

HRID 1432954 reaction equation
C([O-])(=O)C.[NH4+:5].C1(O)C=CC=CC=1.C1(S([N:22]2[C:30]3[CH:29]=[CH:28][N:27]=[C:26](Cl)[C:25]=3[CH:24]=[C:23]2[CH2:32][N:33]2[CH2:38][CH2:37][N:36]([S:39]([C:42]3[S:46][C:45]4[CH:47]=[C:48]([Cl:51])[CH:49]=[CH:50][C:44]=4[CH:43]=3)(=[O:41])=[O:40])[CH2:35][C:34]2=[O:52])(=O)=O)C=CC=CC=1>>[NH2:5][C:26]1[C:25]2[CH:24]=[C:23]([CH2:32][N:33]3[CH2:38][CH2:37][N:36]([S:39]([C:42]4[S:46][C:45]5[CH:47]=[C:48]([Cl:51])[CH:49]=[CH:50][C:44]=5[CH:43]=4)(=[O:41])=[O:40])[CH2:35][C:34]3=[O:52])[NH:22][C:30]=2[CH:29]=[CH:28][N:27]=1

Participants

4

Reactant 3

HCID 996PhenolHCID 517165Ammonium AcetateHCID 57170552HCID 57170552, compound

Product 1

HCID 11049045HCID 11049045, compound

Conditions

Temperature
100 °C

Procedure

Anhydrous ammonium acetate (0.56 g, 7.2 mmol), phenol (0.45 g, 4.8 mmol) and 1-(1-benzenesulfonyl-4-chloro-1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-piperazin-2-one (0.31 g, 0.48 mmol, prepared as described previously) are heated to 100° C. for 3.5 days. The mixture is cooled to RT then the crude product is purified by RP-HPLC eluting in a gradient of 10% CH3CN/H2O (0.1% TFA) to 100% CH3CN then the appropriate product fractions are lyophilized to provide the title compound (1.29 g, 2.2 mmol) as a white solid (22.4 mg, 0.038 mmol). 1H NMR (DMSO-d6, 300 MHz) δ12.40 (bs, 1H), 12.00 (bs, 1H), 8.31 (d, 1H), 8.20 (s, 1H), 8.06 (d, 1H), 8.02 (bs, 2H), 7.57 (dd, 1H), 7.48 (m, 1H), 6.89 (d, 1H), 6.81 (s, 1H), 4.60 (s, 1H), 3.81 (s, 2H), 3.40 (m, 4H). LR-FAB MS, [M+H]+=476, 478.

Workup

  1. temperatureThe mixture is cooled to RT
  2. customthe crude product is purified by RP-HPLC
  3. washeluting in a gradient of 10% CH3CN/H2O (0.1% TFA) to 100% CH3CN

Sources & evidence

ORD record
ord-5828a969ad7f4f2f882647b3e7ec0bed
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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