Formaldehyde → Ethyl 1-[5-[7-bromo-2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate

HRID 712178Notes

Reaction equation

[Br:1][C:2]1[C:10]2[S:9][C:8]([NH:11][C:12](=[O:16])[NH:13][CH2:14][CH3:15])=[N:7][C:6]=2[CH:5]=[C:4]([C:17]2[CH:18]=[N:19][C:20]([N:23]3[CH2:28][CH2:27][C:26]([CH3:34])([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:25][CH2:24]3)=[N:21][CH:22]=2)[CH:3]=1.[CH3:35][N:36]1[CH2:41]COC[CH2:37]1.C=O.CN>CCO>[Br:1][C:2]1[C:10]2[S:9][C:8]([N:11]3[CH2:37][N:36]([CH3:41])[CH2:35][N:13]([CH2:14][CH3:15])[C:12]3=[O:16])=[N:7][C:6]=2[CH:5]=[C:4]([C:17]2[CH:18]=[N:19][C:20]([N:23]3[CH2:28][CH2:27][C:26]([CH3:34])([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:25][CH2:24]3)=[N:21][CH:22]=2)[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Ethyl 1-[5-[7-bromo-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (3.11 g, 5.68 mmol) was suspended in EtOH (120 mL). To the stirred suspension was added, NMM (3.1 mL, 28.4 mmol), aqueous formaldehyde (4.61 mL, 56.8 mmol) and methylamine solution (14.2 mL, 28.4 mmol). The reaction mixture was then stirred at 80° C. for 16 h. The reaction mixture was cooled to rt and filtered. The precipitate was washed with EtOH, Et2O and dried to afford the desired compound (2.58 g, 75%) as an off-white solid. m/z=602.09 and 604.02 [M+H]+.

Workup

additionTo the stirred suspension was added
temperatureThe reaction mixture was cooled to rt
filtrationfiltered
washThe precipitate was washed with EtOH, Et2O
customdried

Sources & evidence

ORD record: ord-c5507269f97e4c7cb375f85501c1fae7
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181234B2

Reaction notes

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