Triethylamine → HCID 22475355, compound

HRID 2184213Notes

Reaction equation

HRID 2184213 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, 10H), 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-d6d6a8bd188447ffbdea1362de165164
Source dataset
uspto-grants-2005_05
Patent number
US06900231B2

Reaction notes

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