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Diisopropylethylamine → N-[4-methyl-5-(5-{[(1-methylpiperidin-4-yl)amino]sulfonyl}-2-thienyl)-1,3-thiazol-2-yl]acetamide

HRID 1948396
Notes
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Reaction equation

HRID 1948396 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[S:15][C:14]([S:16](Cl)(=[O:18])=[O:17])=[CH:13][CH:12]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].[NH2:20][CH:21]1[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]1.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[CH3:10][C:8]1[N:9]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[S:6][C:7]=1[C:11]1[S:15][C:14]([S:16]([NH:20][CH:21]2[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]2)(=[O:18])=[O:17])=[CH:13][CH:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27375314-Amino-1-methylpiperidineHCID 866225625-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride

Product 1

HCID 11998304N-[4-methyl-5-(5-{[(1-methylpiperidin-4-yl)amino]sulfonyl}-2-thienyl)-1,3-thiazol-2-yl]acetamide

Reagents, catalysts & solvents 1

HCID 22350042
dichloromethane N,N-dimethylformamide
Solvent

Procedure

5-[2-(acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride, prepared as in Step I of Example 9 (110 mg; 0.33 mmol; 1 eq.), is dissolved in a mixture of DCM/DMF (1/1, 10 ml). 4-Amino-1-methylpiperidine (188 mg; 1.65 mmol; 5 eq.) and DIEA (0.17 ml; 0.98 mmol; 3 eq.) are added. After 3 hours, the solvents are evaporated. The crude product is dissolved in DCM and washed with NH4C1 saturated solution, water and dried over MgSO4. After evaporation of the solvents, crude material is dissolved in DCM (3 ml) and title compound precipitated with Et2O affording after filtration, compound (4) as a white powder (120 mg; 90%). 1H NMR (DMSO-d6) δ 1.25 (m, 2H), 1.55 (m, 2H), 1.80 (m, 2H), 2.05 (m, 2H), 2.25 (s, 6H), 2.40 (s, 3H), 3.05 (m, 1H), 6.95 (d, J=3 Hz, 1H), 7.52 (d, J=3 Hz, 1H), 12.23 (m, 1H). M− (ESI): 413.30; M+ (ESI): 415.30. HPLC, Rt: 2.08 min (purity: 99.33%).

Workup

  1. customthe solvents are evaporated
  2. dissolutionThe crude product is dissolved in DCM
  3. washwashed with NH4C1 saturated solution, water
  4. dry with materialdried over MgSO4
  5. customAfter evaporation of the solvents, crude material
  6. dissolutionis dissolved in DCM (3 ml)
  7. customtitle compound precipitated with Et2O affording
  8. filtrationafter filtration, compound (4) as a white powder (120 mg; 90%)

Sources & evidence

ORD record
ord-cfc81861c70042e6b8ac60bd8bbca7aa
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08399497B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes