Triethylamine → HCID 57448322, compound

HRID 547357Notes

Reaction equation

HRID 547357 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:19]=[CH:18][C:7]([O:8][C:9]2[S:10][C:11]3[C:16]([N:17]=2)=[CH:15][CH:14]=[CH:13][N:12]=3)=[CH:6][CH:5]=1.[NH:20]1[CH2:25][CH2:24][CH:23]([N:26]2[CH2:30][CH2:29][CH2:28][C:27]2=[O:31])[CH2:22][CH2:21]1.CCN(CC)CC>CC#N>[N:17]1[C:16]2[C:11](=[N:12][CH:13]=[CH:14][CH:15]=2)[S:10][C:9]=1[O:8][C:7]1[CH:18]=[CH:19][C:4]([CH2:3][N:20]2[CH2:21][CH2:22][CH:23]([N:26]3[CH2:30][CH2:29][CH2:28][C:27]3=[O:31])[CH2:24][CH2:25]2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 183142501-(Piperidin-4-yl)pyrrolidin-2-oneHCID 57448400HCID 57448400, compound

Product 1

HCID 57448322HCID 57448322, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-[4-(chloromethyl)phenoxy][1,3]thiazolo[5,4-b]pyridine hydrochloride (70 mg, 0.223 mmol) and 1-piperidin-4-yl-pyrrolidin-2-one (64 mg, 0.379 mmol, 1.7 equiv.) in CH3CN (1.3 mL) was added Et3N (110 μL, 0.759 mmol, 3.4 equiv.). The reaction was allowed to stir at 60° C. for 6 h. The solution was cooled to rt, filtered and purified using preparative reverse phase HPLC to afford the desired product as a cream-colored solid (52 mg, 57%). 1H NMR (600 MHz, DMSO-d6): 8.45 (dd, J=4.7, 1.5, 1H), 8.09 (dd, J=8.1, 1.5, 1H), 7.50 (dd, J=8.2, 4.8, 1H), 7.47-7.40 (m, 4H), 3.80-3.69 (m, 1H), 3.52 (s, 2H), 3.35-3.29 (m, 2H), 2.91-2.85 (m, 2H), 2.20 (t, J=8.1, 2H), 2.07-2.00 (m, 2H), 1.94-1.85 (m, 2H), 1.73-1.62 (m, 2H), 1.54-1.48 (m, 2H). MS (ESI): mass calcd. for C22H24N4O2S, 408.16; m/z found, 409.2 [M+H]+.

Workup

  1. temperatureThe solution was cooled to rt
  2. filtrationfiltered
  3. custompurified

Sources & evidence

ORD record
ord-48850166a7af4bfeacb277554db98d4d
Source dataset
uspto-grants-2011_05
Patent number
US07939527B2

Reaction notes

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