Pyridine → HCID 67276225, compound

HRID 1698069Notes

Reaction equation

HRID 1698069 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[S:21][C:22]4[CH:28]=[C:27]([NH2:29])[CH:26]=[CH:25][C:23]=4[N:24]=3)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:30][S:31](Cl)(=[O:33])=[O:32].N1C=CC=CC=1>C(Cl)Cl>[CH3:30][S:31]([NH:29][C:27]1[CH:26]=[CH:25][C:23]2[N:24]=[C:20]([C:17]3[CH:18]=[CH:19][C:14]([N:11]4[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][CH2:12]4)=[N:15][CH:16]=3)[S:21][C:22]=2[CH:28]=1)(=[O:33])=[O:32]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 57553404HCID 57553404, compound

Product 1

HCID 67276225HCID 67276225, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-[5-(6-amino-benzothiazol-2-yl)-pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester (12.7 mg, 0.031 mmol) in DCM (1 mL) was added methanesulfonyl chloride (3 μL, 0.034 mmol) followed by pyridine (3 μL, 0.034 mmol). The r.m. was stirred o.n. at r.t. The crude mixture was purified by flash column chromatography (heptane:ethyl acetate; 50:50 to 40:60), to give intermediate tert-butyl 4-(5-{6-[(methylsulfonyl)amino]-1,3-benzothiazol-2-yl}pyridin-2-yl)piperazine-1-carboxylate (7.4 mg) as a solid. MS m/z (M+H) 490, (M−H) 488. This intermediate was dissolved in DCM (1 mL) and TFA (300 μL) was added. The reaction mixture was thereafter stirred for three hours at r.t. The solvent was removed in a stream of nitrogen and the residue was dissolved in DMF (400 μL) and purified by prep. HPLC, to give the title compound (3 mg) as a white solid. 1H NMR δ 8.71 (d, 1H) 8.09 (dd, 1H) 7.72-7.86 (m, 2H) 7.27 (dd, 1H) 6.88 (d, 1H) 3.63-3.77 (m, 4H) 2.95-3.08 (m, 4H) 2.90 (s, 3H); MS m/z M+H 390, M−H 388.

Workup

  1. customat r.t
  2. customThe crude mixture was purified by flash column chromatography (heptane:ethyl acetate; 50:50 to 40:60)

Sources & evidence

ORD record
ord-cdd5d1d47e554f37a757eba97189dbe7
Source dataset
uspto-grants-2012_04
Patent number
US08163928B2

Reaction notes

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