Dimethylamine → HCID 58880080, compound

HRID 1882238Notes

Reaction equation

HRID 1882238 reaction equation
CS(Cl)(=O)=O.[CH2:6]([S:8]([C:11]1[CH:12]=[C:13]([C:17]2[CH:25]=[C:24]([CH2:26]O)[CH:23]=[C:22]3[C:18]=2[C:19]2[CH:31]=[C:30]([CH3:32])[CH:29]=[N:28][C:20]=2[NH:21]3)[CH:14]=[CH:15][CH:16]=1)(=[O:10])=[O:9])[CH3:7].[CH:33]([N:36](C(C)C)[CH2:37]C)(C)C.CNC>C1COCC1>[CH2:6]([S:8]([C:11]1[CH:12]=[C:13]([C:17]2[CH:25]=[C:24]([CH2:26][N:36]([CH3:37])[CH3:33])[CH:23]=[C:22]3[C:18]=2[C:19]2[CH:31]=[C:30]([CH3:32])[CH:29]=[N:28][C:20]=2[NH:21]3)[CH:14]=[CH:15][CH:16]=1)(=[O:10])=[O:9])[CH3:7]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58880163HCID 58880163, compound

Product 1

HCID 58880080HCID 58880080, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methanesulfonyl chloride (18 μL, 0.24 mmol) was added to a solution of Compound 133 (46 mg, 0.12 mmol) and diisopropylethylamine (43 μL, 0.25 mmol) in THF (1 mL) at 0° C. After stirring for 3 h, dimethylamine (2M, 1 mL, 2 mmol) was added, and the reaction stirred for 16 h. The solution was concentrated in vacuo and purified by prep-HPLC to give 32 mg (65%) of the title compound as a pale yellow oil. 1H NMR (400 MHz, CD3OD) δ 8.36 (br s, 1H), 8.22 (s, 1H), 8.13 (d, 1H, J=7.6 Hz), 8.05 (d, 1H, J=7.6 Hz), 7.88-7.94 (m, 2H), 7.85 (s, 1H), 7.44 (s, 1H), 4.57 (s, 2H), 3.33 (q, 2H, J=7.2 Hz), 2.94 (s, 6H), 2.39 (s, 3H), 1.30 (t, 3H, J=7.2 Hz). MS (ES) [m+H] calc'd for C23H25N3O2S, 408; found 408.

Workup

  1. stirringthe reaction stirred for 16 h
  2. concentrationThe solution was concentrated in vacuo
  3. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-90ba9a26732e49c39eef49969f32d3e3
Source dataset
uspto-grants-2012_11
Patent number
US08318939B2

Reaction notes

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