Diisopropylethylamine → HCID 86664014, compound

HRID 712298Notes

Reaction equation

HRID 712298 reaction equation
Cl.[F:2][C:3]([F:16])([F:15])[C:4]1([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.CCN(C(C)C)C(C)C.Cl[C:27]1[N:32]=[CH:31][C:30]([C:33]2[CH:34]=[C:35]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][N:49]=3)[C:36]3[S:40][C:39]([NH:41][C:42]([NH:44][CH2:45][CH3:46])=[O:43])=[N:38][C:37]=3[CH:47]=2)=[CH:29][N:28]=1>CC(N(C)C)=O>[CH2:45]([NH:44][C:42](=[O:43])[NH:41][C:39]1[S:40][C:36]2[C:35]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][N:49]=3)=[CH:34][C:33]([C:30]3[CH:31]=[N:32][C:27]([N:7]4[CH2:6][CH2:5][C:4]([C:3]([F:2])([F:15])[F:16])([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:9][CH2:8]4)=[N:28][CH:29]=3)=[CH:47][C:37]=2[N:38]=1)[CH3:46]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 66977111HCID 66977111, compoundHCID 86663958HCID 86663958, compound

Product 1

HCID 86664014HCID 86664014, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To the solution of ethyl 4-(trifluoromethyl)piperidine-4-carboxylate hydrochloride (0.1 g, 0.44 mmol) in DMA (5.0 mL) was added DIPEA (0.25 mL, 1.46 mmol) at rt and the mixture stirred at rt for 10 min followed by addition of 1-(5-(2-chloropyrimidin-5-yl)-7-(pyridin-2-yl)benzothiazol-2-yl)-3-ethylurea (0.12 g, 0.29 mmol). The reaction was heated up to 80° C. for 16 h and after completion (by TLC), the mixture was poured into 50 mL of ice cold water, extracted with EtOAc (3×50 mL) and the combined organics washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude residue was purified over 100-200 M silica-gel using 1.50% MeOH: DCM to obtain an off white solid (0.09 g, 51%). 1H NMR (DMSO-d6): δ 1.15 (t, J=7.20 Hz, 3H), 1.20 (t, J=6.80 Hz, 3H), 1.45 (m, 2H), 2.06 (m, 2H), 2.54 (m, 2H), 3.21 (q, J=7.20, 2H), 4.15 (q, J=6.80 Hz, 2H), 4.32 (m, 2H), 6.86 (br s, 1H), 7.44 (m, 1H), 7.99 (m, 2H), 8.23 (s, 1H), 8.47 (m, 1H), 8.80 (m, 1H), 8.92 (s, 2H) and 10.56 (br s, 1H).

Workup

  1. temperatureThe reaction was heated up to 80° C. for 16 h
  2. extractionextracted with EtOAc (3×50 mL)
  3. washthe combined organics washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified over 100-200 M silica-gel

Sources & evidence

ORD record
ord-47ca282b109245a79c7a98e0a9195941
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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