Methanesulfonyl chloride → (4-Isopropyl-piperazin-1-yl)-(2-piperidin-1-ylmethyl-thiazol-4-yl)-methanone

HRID 33747Notes

Reaction equation

[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[N:13]=[C:14]([CH2:17]OS(C)(=O)=O)[S:15][CH:16]=2)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].OCC1S[CH:27]=[C:28]([C:30]([N:32]2[CH2:37][CH2:36]N(C(C)C)CC2)=O)N=1.CS(Cl)(=O)=O>C(Cl)Cl>[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[N:13]=[C:14]([CH2:17][N:32]3[CH2:30][CH2:28][CH2:27][CH2:36][CH2:37]3)[S:15][CH:16]=2)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

Methanesulfonic acid 4-(4-isopropyl-piperazine-1-carbonyl)-thiazol-2-ylmethyl ester. (2-Hydroxymethyl-thiazol-4-yl)-(4-isopropyl-piperazin-1-yl)-methanone (0.95 g. 3.5 mmol) and TEA (0.542 mL, 3.89 mmol) were suspended in DCM (50 mL). The suspension was cooled to 0° C. and methanesulfonyl chloride (0.3 mL) was added dropwise. The mixture was stirred at 0° C. for 30 min, then warmed to rt and stirred for 2 h. The mixture was concentrated at rt to yield the title compound (0.50 g, 41%). The crude mesylate was carried forward to the next step. MS (ESI): exact mass calcd. for C14H22N2O4S2, 347.10; m/z found, 348.5 [M+H]+.

Workup

temperaturewarmed to rt
stirringstirred for 2 h
concentrationThe mixture was concentrated at rt

Sources & evidence

ORD record: ord-a6507477f36049189ea70ef4e5da4d0a
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429659B2

Reaction notes

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