Pyridine → HCID 10598750, compound

HRID 1734034Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([N:8]([CH2:29][CH3:30])[CH2:9][CH2:10][N:11]1[C:19]2[CH:18]=[CH:17][C:16]([CH2:20][NH2:21])=[C:15]3[S:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:13]([C:14]=23)=[N:12]1)[CH3:7].N1C=CC=CC=1.[OH-].[Na+]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:29]([N:8]([CH2:6][CH3:7])[CH2:9][CH2:10][N:11]1[C:19]2[CH:18]=[CH:17][C:16]([CH2:20][NH:21][S:2]([CH3:1])(=[O:4])=[O:3])=[C:15]3[S:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:13]([C:14]=23)=[N:12]1)[CH3:30]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methanesulfonyl chloride (0.172 g, 1.50 mmol) in CH2Cl2 (30 mL) is added the freebase of the compound of example 8 (0.51 g, 1.28 mmol)) and pyridine (0.4 mL) with stirring at 0° C. After the mixture is allowed to warm to ambient temperature over 5h CHCl3 (30 mL) and 2N NaOH (5 mL) is added to the mixture. The organic layers are separated, washed with water, dried over Na2SO4, and concentrated in vacuo to give the crude product. Purification by chromatography with 0.5% Et3N in CH2Cl2 gives 0.650 g of gum. Recrystallization from ether-methanol (90:10) gives the compound (0.460 g, 84%), mp: 120°-125° C. 1H NMR (CDCl3) 0.98 (6H; t), 2.58 (4H; q), 2.84 (3H; s), 2.92 (2H; t), 4.26 (2H; d), 4.38 (2H; t), 4.48 (1H; b), 6.90 (1H; d), 7.08-7.30 (4H; m), 8.06 (1H; m)ppm. MS m/z 431 (MH+). Anal. (C21H26N4O2S2.1/2H2O) C, H, N.

Workup

additionis added to the mixture
customThe organic layers are separated
washwashed with water
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customto give the crude product
customPurification by chromatography with 0.5% Et3N in CH2Cl2

Sources & evidence

ORD record: ord-341ed26e020847c08c433d1e71a6d152
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05532263

Reaction notes

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