Triethylamine → HCID 22475355, compound

HRID 1060231Notes

Reaction equation

HRID 1060231 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=2)(=[O:11])=[O:10])=[C:4]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:3]=1[CH2:27][CH:28]=C.F[P-](F)(F)(F)(F)F.N1([O:46][P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.Cl.[NH2:66][C:67]1[CH:72]=[CH:71][C:70]([CH2:73][NH2:74])=[C:69]([CH3:75])[N:68]=1>CN(C=O)C.C(Cl)Cl>[NH2:66][C:67]1[N:68]=[C:69]([CH3:75])[C:70]([CH2:73][NH:74][C:28](=[O:46])[CH2:27][C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[C:5]([NH:8][S:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=3)(=[O:11])=[O:10])[C:4]=2[O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:71][CH:72]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 22475359[4-Methyl-2-(phenylmethoxy)-3-prop-2-enylphenyl][(3-methylphenyl)sulfonyl]amineHCID 665242322-Amino-5-aminomethyl-6-methylpyridine dihydrochloride

Product 1

HCID 22475355HCID 22475355, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The product of Example 9, step 7 (0.18 g, 0.42 mmol), BOP (0.21 g, 0.47 mmol), triethylamine (0.25 mL, 1.80 mmol), and 2-amino-5-aminomethyl-6-methylpyridine dihydrochloride (Sanderson, P. E., et al. WO 97/01338 (1997)) (0.10 g, 0.48 mmol), were dissolved in DMF (10 mL) and stirred at ambient temperature for 2 hours. The reaction was concentrated in vacuo and the crude product purified by flash column chromatography (gradient elution: 10% to 15% methanol in DCM) giving an impure product that was dissolved in DCM, washed with saturated sodium bicarbonate, water, and brine, dried over sodium sulfate, and filtered. The evaporated filtrate then gave the title compound as a pale yellow solid (0.23 g, 99%). 1H NMR (300 MHz, CDCl3) δ 7.64 (m, 1H), 7.56 (m, 1H), 7.35 (m, 1OH), 7.11 (d, 1H, J=8.3 Hz), 6.94 (d, 1H, J=8.5 Hz), 6.22 (d, 1H, J=8.1 Hz), 5.60 (br t, 1H, J=5.3 Hz), 4.49 (s, 2H), 4.37 (br s, 2H), 4.19 (d, 2H, J=5.5 Hz), 3.56 (s, 2H), 2.34 (s, 3H), 2.23 (s, 3H), 2.22 (s, 3H). Mass spectrum (LCMS, ESI pos.) calc'd. for C30H32N4O4S: 545.2 (M+H). Found: 545.2.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe crude product purified by flash column chromatography (gradient elution: 10% to 15% methanol in DCM)
  3. customgiving an impure product that
  4. washwashed with saturated sodium bicarbonate, water, and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-28711e3b454b445bad0190129d83395d
Source dataset
uspto-grants-2003_02
Patent number
US06521663B2

Reaction notes

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