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

HRID 712323Notes

Reaction equation

HRID 712323 reaction equation
N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:25]I.[CH2:27]([N:29]1[CH2:34][N:33]([CH3:35])[CH2:32][N:31]([C:36]2[S:37][C:38]3[C:44]([CH2:45]O)=[CH:43][C:42]([C:47]4[CH:48]=[N:49][C:50]([N:53]5[CH2:58][CH2:57][C:56]([CH3:64])([C:59]([O:61][CH2:62][CH3:63])=[O:60])[CH2:55][CH2:54]5)=[N:51][CH:52]=4)=[CH:41][C:39]=3[N:40]=2)[C:30]1=[O:65])[CH3:28]>C(Cl)Cl>[CH2:27]([N:29]1[CH2:34][N:33]([CH3:35])[CH2:32][N:31]([C:36]2[S:37][C:38]3[C:44]([CH2:45][I:25])=[CH:43][C:42]([C:47]4[CH:48]=[N:49][C:50]([N:53]5[CH2:58][CH2:57][C:56]([CH3:64])([C:59]([O:61][CH2:62][CH3:63])=[O:60])[CH2:55][CH2:54]5)=[N:51][CH:52]=4)=[CH:41][C:39]=3[N:40]=2)[C:30]1=[O:65])[CH3:28]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 66977202Ethyl 1-[5-[2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-7-(hydroxymethyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate

Product 1

HCID 66977298Ethyl 1-[5-[2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-7-(iodomethyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylateYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Imidazole (75 mg, 1.09 mmol), triphenylphosphine (276 mg, 1.05 mmol) and iodine (267 mg, 1.05 mmol) were dissolved in CH2Cl2 (15 mL) and stirred at rt for 5 mins. A solution of ethyl 1-[5-[2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-7-(hydroxymethyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (485 mg, 0.88 mmol) in CH2Cl2 (10 mL) was then added and the mixture stirred at rt for 2 h. The mixture was pre-adsorbed onto silica gel and purified by flash column chromatography (80 g GraceResolv silica cartridge—dry loaded) eluting with 25-100% EtOAc/heptane to afford the desired compound (323 mg, 56%) as a pale yellow foam. MS: 664.02 [M+H]+.

Workup

  1. stirringthe mixture stirred at rt for 2 h
  2. custompurified by flash column chromatography (80 g GraceResolv silica cartridge—dry loaded)
  3. washeluting with 25-100% EtOAc/heptane

Sources & evidence

ORD record
ord-dafd75ae9cc146c58ed7291543d12b98
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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