4-Chlorobenzenesulfonyl chloride → HCID 45381507, compound

HRID 2176183Notes

Reaction equation

HRID 2176183 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH:11]4[CH2:16][CH2:15][N:14]([C:5]=3[C:4]=2[CH:3]=1)[CH2:13][CH2:12]4.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([N:7]2[C:8]3[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][C:4]=3[C:5]3[N:14]4[CH2:15][CH2:16][CH:11]([C:6]2=3)[CH2:12][CH2:13]4)(=[O:26])=[O:25])=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 67544486HCID 67544486, compound

Product 1

HCID 45381507HCID 45381507, compound

Procedure

The coupling of 8-methyl-2,3,4,5-tetrahydro-1,4-ethanopyrido[3,2-b]indole (20 mg, 0.09 mmol; Example 211) and 4-chlorobenzenesulfonyl chloride (30 mg, 0.14 mmol; Aldrich) was performed according to the procedure described in Example 69, except that the product was purified by reverse-phase HPLC [Waters XBridge RP18 column, 5 μm, 30×100 mm, flow rate 40 mL/minute, 20-99% gradient of methanol in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to afford the title compound: 1H NMR (300 MHz, methanol-d4) δ ppm 1.42-1.60 (m, 2H), 1.92-2.13 (m, 2H), 2.40 (s, 3H), 2.45-2.61 (m, 2H), 3.13-3.27 (m, 2H), 4.08 (quintet, J=2.9 Hz, 1H), 7.14 (dd, J=8.6, 1.5 Hz, 1H), 7.35 (s, 1H), 7.46-7.55 (m, 2H), 7.76-7.87 (m, 2H), 8.01 (d, J=8.5 Hz, 1H); MS (ESI) m/z 387 (M+H)+.

Workup

  1. customwas purified by reverse-phase HPLC [Waters XBridge RP18 column, 5 μm, 30×100 mm, flow rate 40 mL/minute, 20-99% gradient of methanol in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)]

Sources & evidence

ORD record
ord-93e3fa0614b34c2d9fa826c6be99331d
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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