Benzenesulfonyl chloride → HCID 11348903, compound

HRID 2102801Notes

Reaction equation

HRID 2102801 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[C:13]3[N:12]=[C:11]([NH2:14])[N:10]=[CH:9][C:8]=3[CH2:7][CH2:6][C:5]=2[N:15]=1.[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>N1C=CC=CC=1>[CH3:1][C:2]1[S:3][C:4]2[C:13]3[N:12]=[C:11]([NH:14][S:22]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)(=[O:24])=[O:23])[N:10]=[CH:9][C:8]=3[CH2:7][CH2:6][C:5]=2[N:15]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 112874152-methyl-4,5-dihydro-[1,3]thiazolo[4,5-h]quinazolin-8-amine

Product 1

HCID 11348903HCID 11348903, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Under anhydrous conditions pyridine (5 mL) was added to 2-methyl-4,5-dihydro-thiazolo[4,5-h]quinazolin-8-ylamine (148 mg, 0.68 mmol). The mixture was stirred at 60° C. for 1 h before benzenesulfonyl chloride (121 μL, 168 mg, 0.95 mmol) was added. After 16 h the mixture was cooled and evaporated to dryness. Flash column chromatography (20% EtOAc:hexane) gave the title product as a tan solid (86 mg, 35%): mp 265° C. (dec). Anal. RP-HPLC: tR 15.5 min (0-60% MeCN, purity 100%). 1H-NMR (DMSO-d6): δ 8.25 (s, 1H, Py-H), 8.03-7.98 (m, 2H, Ph-H), 7.62-7.55 (m, 3H, Ph-H), 2.92 (m, 4H, CH2—CH2), 2.73 (s, 3H, CH3). 13C-NMR (DMSO-d6): δ 170.15, 160.04, 156.92, 155.66, 153.95, 140.76, 132.51, 128.60, 127.70, 126.97, 118.96, 24.35, 22.94, 19.51. MS (ESI+): m/z 380.97 (M+Na)+.

Workup

  1. additionwas added
  2. temperatureAfter 16 h the mixture was cooled
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-c7dddd5a1ce3463fa88dbfe1d065c46e
Source dataset
uspto-grants-2009_08
Patent number
US07576091B2

Reaction notes

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