Triethylamine → HCID 86701993, compound

HRID 715811Notes

Reaction equation

HRID 715811 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12]([C:14]3[S:18][C:17]([CH:19]4[CH2:23][CH2:22][NH:21][CH2:20]4)=[N:16][CH:15]=3)=[O:13])=[CH:6][C:5]=12.C(N(CC)CC)C.[CH3:31][CH:32]([CH3:38])[CH2:33][S:34](Cl)(=[O:36])=[O:35]>CN(C)C=O.O>[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12]([C:14]3[S:18][C:17]([CH:19]4[CH2:23][CH2:22][N:21]([S:34]([CH2:33][CH:32]([CH3:38])[CH3:31])(=[O:36])=[O:35])[CH2:20]4)=[N:16][CH:15]=3)=[O:13])=[CH:6][C:5]=12

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1822361-Propanesulfonyl chloride, 2-methyl-HCID 86701994HCID 86701994, compound

Product 1

HCID 86701993HCID 86701993, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(pyrrolidin-3-yl)thiazole-5-carboxamide, 2.7-trifluoroacetic acid (150 mg, 0.236 mmol) was dissolved in N,N-dimethylformamide (0.7 mL). Triethylamine (0.3 mL, 2.152 mmol) was added, followed by 2-methylpropane-1-sulfonyl chloride (74.0 mg, 0.472 mmol) and the reaction was stirred overnight at room temperature. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic extracts were dried with sodium sulfate, filtered, and concentrated and purified by normal phase chromatography to give the title compound. 1H NMR (300 MHz, DMSO-d6). δ ppm 9.24 (t, J=5.9 Hz, 1H), 8.49 (d, J=7.0 Hz, 1H), 8.35 (s, 1H), 7.89 (s, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.41 (s, 1H), 6.83 (dd, J=7.0, 1.7 Hz, 1H), 4.48 (d, J=5.9 Hz, 2H), 3.91 (p, J=7.2 Hz, 1H), 3.74 (dd, J=9.8, 7.3 Hz, 1H), 3.51-3.35 (m, 3H), 2.99 (d, J=6.6 Hz, 2H), 2.46-2.33 (m, 1H), 2.24-2.03 (m, 2H), 1.03 (d, J=6.7 Hz, 6H); MS (ESI(+)) m/e 448 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic extracts were dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by normal phase chromatography

Sources & evidence

ORD record
ord-fa0bb7ce2239444bbc932d9bba3239d9
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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