Diisopropylethylamine → HCID 178437149, compound

HRID 710171Notes

Reaction equation

HRID 710171 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:14]=[C:13]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:12]=[CH:11][C:10]=1[C:19]1[NH:23][C:22]2[CH:24]=[CH:25][C:26]([CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[CH:27][C:21]=2[N:20]=1.Cl[C:35]1[N:40]=[CH:39][C:38]([CH2:41][CH3:42])=[CH:37][N:36]=1.CCN(C(C)C)C(C)C>CC(O)C>[CH2:41]([C:38]1[CH:37]=[N:36][C:35]([N:31]2[CH2:32][CH2:33][CH:28]([C:26]3[CH:25]=[CH:24][C:22]4[NH:23][C:19]([C:10]5[CH:11]=[CH:12][C:13]([S:15]([CH3:18])(=[O:16])=[O:17])=[CH:14][C:9]=5[F:8])=[N:20][C:21]=4[CH:27]=3)[CH2:29][CH2:30]2)=[N:40][CH:39]=1)[CH3:42]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 35727632-Chloro-5-ethylpyrimidineHCID 178504691HCID 178504691, compound

Product 1

HCID 178437149HCID 178437149, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

Example 57 (150 mg, 0.3 mmol) dissolved in DCM (12 ml) and added TFA (0.45 ml). This mixture stirred at rt for 3 h. After 3 h, DCM removed on rotavapour and co-distilled with DCM to obtain 2-[2-fluoro-4-(methylsulfonyl)phenyl]-5-(piperidin-4-yl)-1H-benzo[d]imidazole 2,2,2-trifluoroacetate (150 mg). 2-[2-fluoro-4-(methylsulfonyl)phenyl]-5-(piperidin-4-yl)-1H-benzo[d]imidazole 2,2,2-trifluoroacetate (150 mg, 0.4 mmol) and 2-chloro-5-ethylpyrimidine (60 mg, 0.4 mmol) were dissolved in propan-2-ol (10 ml) and added DiPEA (0.6 ml, 3.2 mmol). This mixture was refluxed at 90° C. for 12 h. After 12 h, propan-2-ol removed on rotavapor to obtain the residue. Residue was purified on combiflash using Ethyl acetate and Petether (1:1) as eluent to afford the titled compound (50 mg) as a white solid. M.P.: 220-223.5° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 12.69 (d, J 12.8, 1H), 8.49-8.45 (m, 1H), 8.24 (s, 2H), 8.00 (dd, J 1.5, 10.4, 1H), 7.91 (d, J 8.3, 1H), 7.67-7.56 (m, 1H), 7.55-7.40 (m, 1H), 7.22-7.12 (m, 1H), 4.80 (d, J 12.6, 2H), 3.33 (s, 3H), 2.97-2.91 (m, 3H), 2.43 (q, J 7.5, 2H), 1.89 (d, J 12.4, 2H), 1.69-1.54 (m, 2H), 1.13 (t, J 7.6, 3H).

Workup

  1. custompropan-2-ol removed on rotavapor
  2. customto obtain the residue
  3. customResidue was purified on combiflash

Sources & evidence

ORD record
ord-d90b63f93d1449ad9e46cc3e089fb750
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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