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 712182Notes

Reaction equation

HRID 712182 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

6

Reactant 4

HCID 712FormaldehydeHCID 6329MethylamineHCID 79724-MethylmorpholineHCID 86663956Ethyl 1-(5-(7-bromo-2-(3-ethylureido)benzo[d]thiazol-5-yl)pyrimidin-2-yl)-4-methylpiperidine-4-carboxylate

Product 1

HCID 66977053Ethyl 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-carboxylateYield 75.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 1-[5-[7-bromo-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (Jubilant) (3.0 g, 5.48 mmol) was suspended in EtOH (120 mL). N-methylmorpholine (3.0 mL, 27.4 mmol), aqueous formaldehyde (4.45 mL, 54.8 mmol) and methylamine solution (2 M) (13.7 mL, 27.4 mmol) were added and the reaction mixture stirred at rt for 16 h, followed by a further 4 hrs at 80° C. The reaction mixture was cooled to rt and the resulting precipitate filtered. The precipitate was washed with EtOH, Et2O and dried using a vacuum oven to afford the desired product (2.5 g, off white solid).

Workup

  1. waitfollowed by a further 4 hrs at 80° C
  2. temperatureThe reaction mixture was cooled to rt
  3. filtrationthe resulting precipitate filtered
  4. washThe precipitate was washed with EtOH, Et2O
  5. customdried

Sources & evidence

ORD record
ord-1ee4d692b89b41a585d20162d27db606
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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