Triethylamine → HCID 86664040, compound

HRID 712329Notes

Reaction equation

[CH2:1]([C:3]1([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:8][CH2:7][N:6]([C:9]2[N:14]=[CH:13][C:12]([C:15]3[CH:16]=[C:17]([C:34]#[C:35][CH2:36][OH:37])[C:18]4[S:22][C:21]([N:23]5[CH2:28][N:27]([CH3:29])[CH2:26][N:25]([CH2:30][CH3:31])[C:24]5=[O:32])=[N:20][C:19]=4[CH:33]=3)=[CH:11][N:10]=2)[CH2:5][CH2:4]1)[CH3:2].C(N(CC)CC)C.[CH3:50][S:51](Cl)(=[O:53])=[O:52]>C(Cl)Cl.O>[CH2:1]([C:3]1([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:4][CH2:5][N:6]([C:9]2[N:14]=[CH:13][C:12]([C:15]3[CH:16]=[C:17]([C:34]#[C:35][CH2:36][O:37][S:51]([CH3:50])(=[O:53])=[O:52])[C:18]4[S:22][C:21]([N:23]5[CH2:28][N:27]([CH3:29])[CH2:26][N:25]([CH2:30][CH3:31])[C:24]5=[O:32])=[N:20][C:19]=4[CH:33]=3)=[CH:11][N:10]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

Ethyl 4-ethyl-1-[5-[2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-7-(3-hydroxyprop-1-ynyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylate (325 mg, 0.55 mmol) was dissolved in anhydrous DCM (32 mL) under argon and the solution cooled to 0° C. Triethylamine (0.19 mL, 1.40 mmol) was added followed by methanesulfonyl chloride (0.064 mL, 0.82 mmol) and the mixture allowed to warm to rt and stirred for 45 minutes. The mixture was diluted with water, extracted into DCM (3×20 mL) and the combined organic layer washed with brine, dried over Na2SO4 and concentrated to dryness under reduced pressure. The desired compound was obtained as a yellow oil which was used without further purification in the next step. MS: 670.09 [M+H]+.

Workup

temperatureto warm to rt
extractionextracted into DCM (3×20 mL)
washthe combined organic layer washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record: ord-efa31da40b004565850f6ed45c12b2da
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181234B2

Reaction notes

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