Sodium hydride → HCID 67156766, compound

HRID 549289Notes

Reaction equation

[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([S:11]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)(=[O:13])=[O:12])[S:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[H-].[Na+].[NH:24]1[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25]1>CN(C=O)C>[ClH:1].[CH3:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][S:11]([C:9]2[S:10][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([O:29][CH:26]4[CH2:27][CH2:28][NH:24][CH2:25]4)[C:7]=3[CH:8]=2)(=[O:13])=[O:12])=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 200 °C

Procedure

4-Chloro-N-(4-methylphenyl)thieno[3,2-c]pyridine-2-sulfonamide (60.0 mg, 0.17 mmol) in dry DMF (1 mL) and NaH (5.1 mg, 0.21 mmol) was added to pyrrolidin-3-ol (18.5 mg, 0.21 mmol) under nitrogen. The mixture was heated in the microwave at 200° C. in 5 min. The product was purified by preparative HPLC. Yield: 29.9 mg (43.4%). 1H NMR (270 MHz, CH3OH-d4) δ ppm 8.09 (s, 1H) 7.71 (d, J=6.93 Hz, 1H) 7.46 (d, J=6.93 Hz, 1H) 7.47-7.44 (m, 4H) 4.67 (d, J=3.22 Hz, 1H) 3.97 (s, 2H) 2.26 (s, 3H). LC-MS 390 (M−H)+; Purity (HPLC) 99%.

Workup

customThe product was purified by preparative HPLC

Sources & evidence

ORD record: ord-572fda6cde824d74b8286f3252443ace
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943639B2

Reaction notes

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