1,1'-Carbonyldiimidazole → HCID 86659761, compound

HRID 1889632Notes

Reaction equation

HRID 1889632 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:31]=[CH:32][CH:33]=1)[CH2:6][N:7]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=1)[S:8]([C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[C:12]=1[OH:19])(=[O:10])=[O:9].C(N(CC)C(C)C)(C)C.[C:43](N1C=CN=C1)(N1C=CN=C1)=[O:44].Cl.[Cl:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=1[N:63]1[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]1>CN(C=O)C>[Cl:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=1[N:63]1[CH2:68][CH2:67][N:66]([C:43]([NH:1][CH2:2][C:3]2[CH:33]=[CH:32][CH:31]=[C:5]([CH2:6][N:7]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([C:27]([F:29])([F:28])[F:30])=[CH:25][CH:26]=3)[S:8]([C:11]3[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[C:12]=3[OH:19])(=[O:9])=[O:10])[CH:4]=2)=[O:44])[CH2:65][CH2:64]1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 30170151-(2-Chlorophenyl)piperazinium chlorideHCID 58531583HCID 58531583, compound

Product 1

HCID 86659761HCID 86659761, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(3-(aminomethyl)benzyl)-3,5-dichloro-2-hydroxy-N-(4-(trifluoromethyl)benzyl)benzenesulfonamide (60 mg, 0.12 mmol) in DMF (2 mL) were added N,N-diisopropylethylamine (0.08 mL, 0.46 mmol) and 1,1′-carbonyldiimidazole (20.6 mg, 0.13 mmol). The resulting mixture was stirred at it for 1 h under nitrogen, then 1-(2-chlorophenyl)piperazine monohydrochloride (29.6 mg, 0.13 mmol) was added. The mixture was stirred overnight. The mixture was concentrated and purified by preparative HPLC. Fractions containing the desired product were combined, concentrated and lyophilized to give white solid (54 mg, 62%). 1H NMR (MeOD-d4): δ 7.57 (d, J=2.8 Hz, 1H), 7.52 (d, J=2.8 Hz, 1H), 7.40 (d, J=8.3 Hz, 2H), 7.28 (m, 1H), 7.21 (d, J=8.3 Hz, 2H), 7.15 (m, 1H), 7.06 (m, 4H), 6.92 (m, 1H), 6.88 (m, 1H), 4.45 (s, 2H), 4.41 (s, 2H), 4.21 (s, 2H), 3.50 (t, J=5.0 Hz, 4H), 2.93 (t, J=5.0 Hz, 4H); MS (ESI): (M+H)+=743.2.

Workup

  1. stirringThe mixture was stirred overnight
  2. concentrationThe mixture was concentrated
  3. custompurified by preparative HPLC
  4. additionFractions containing the desired product
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-64f7458159b54895872a0a4533f821c0
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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