1-Benzylpiperazine → HCID 90013542, compound

HRID 1486840Notes

Reaction equation

HRID 1486840 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]4[CH:24]=[CH:23][C:22]([N:25]5[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]5)=[CH:21][CH:20]=4)=[CH:16][CH:17]=3)[C:12]3[C:32](Cl)=[CH:33][CH:34]=[N:35][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:37]([N:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(Cl)Cl>[CH2:37]([N:44]1[CH2:49][CH2:48][N:47]([C:32]2[C:12]3[C:13]4[C:18](=[CH:17][CH:16]=[C:15]([C:19]5[CH:24]=[CH:23][C:22]([N:25]6[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]6)=[CH:21][CH:20]=5)[CH:14]=4)[N:10]([S:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)(=[O:9])=[O:8])[C:11]=3[N:35]=[CH:34][CH:33]=2)[CH2:46][CH2:45]1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

4

Reactant 2

HCID 759941-BenzylpiperazineHCID 72194409HCID 72194409, compound

Product 1

HCID 90013542HCID 90013542, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

9-Benzenesulfonyl-4-chloro-6-[4-(4-methyl-piperazin-1-yl)-phenyl]-9H-pyrido[2,3-b]indole (building block A, 50 mg, 0.0967 mmol) and benzylpiperazine (0.21 mL, 12.5 eq) were heated at 150° C. for 7 h. After cooling to r.t., the reaction mixture was diluted with DCM (20 mL), washed 3 times with water (3×10 mL) and brine (10 mL). The organic layer was dried over MgSO4, filtered and evaporated to dryness. The crude product was purified by silica gel flash chromatography (DCM/MeOH 100:0 to 98:2) to afford the desired product in 57% yield (36.1 mg) as an uncoloured amorphous solid. 1H NMR (300 MHz, CDCl3) δ 8.52 (d, J=8.7 Hz, 1H), 8.40 (d, J=5.6 Hz, 1H), 8.16 (d, J=8.8 Hz, 2H), 8.07 (d, J=1.9 Hz, 1H), 7.71 (dd, J=8.8, 1.9 Hz, 1H), 7.58 (d, J=8.7 Hz, 2H), 7.49 (t, J=7.4 Hz, 1H), 7.40 (d, J=8.0 Hz, 2H), 7.38-7.27 (m, 5H), 7.07 (d, J=8.8 Hz, 2H), 6.82 (d, J=5.6 Hz, 1H), 3.64 (s, 2H), 3.36-3.31 (m, 4H), 3.30-3.18 (m, 4H), 2.88-2.68 (m, 4H), 2.68-2.60 (m, 4H), 2.40 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 155.3 (C), 152.9 (C), 150.6 (C), 147.9 (CH), 138.9 (C), 137.8 (C), 136.8 (C), 135.6 (C), 133.8 (CH), 132.2 (C), 129.2 (CH), 128.9 (CH), 128.5 (CH), 127.9 (CH), 127.7 (CH), 127.4 (CH), 125.8 (CH), 123.1 (C), 120.7 (CH), 116.3 (CH), 114.7 (CH), 110.4 (C), 108.5 (CH), 63.1 (CH2), 55.2 (2CH2), 53.0 (2CH2), 50.6 (2CH2), 49.0 (2CH2), 46.3 (NCH3); MS (ESI) m/z: 657.3 [M+H]+; 1314.7 [2M+H]+; 516.5 [M-SO2Ph+H]′.

Workup

  1. washwashed 3 times with water (3×10 mL) and brine (10 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude product was purified by silica gel flash chromatography (DCM/MeOH 100:0 to 98:2)

Sources & evidence

ORD record
ord-cba47429e8b8443a9900d99184de889d
Source dataset
uspto-grants-2016_08
Patent number
US09428500B2

Reaction notes

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