Diethylene Glycol Monomethyl Ether → HCID 22273532, compound

HRID 1064334Notes

Reaction equation

HRID 1064334 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7]O.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH3:23][N:24]1[C:28]([C:29]2[CH:34]=[CH:33][N:32]=[C:31]([NH:35][C:36]3[CH:41]=[CH:40][C:39]([S:42](=[O:52])(=[O:51])[NH:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[CH:38][CH:37]=3)[N:30]=2)=[CH:27][N:26]=[C:25]1[CH3:53].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:23][N:24]1[C:28]([C:29]2[CH:34]=[CH:33][N:32]=[C:31]([NH:35][C:36]3[CH:37]=[CH:38][C:39]([S:42](=[O:52])(=[O:51])[N:43]([C:44]([O:46][C:47]([CH3:49])([CH3:50])[CH3:48])=[O:45])[CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:40][CH:41]=3)[N:30]=2)=[CH:27][N:26]=[C:25]1[CH3:53]

Participants

6

Reactant 4

HCID 8134Diethylene Glycol Monomethyl EtherHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 22273497HCID 22273497, compound

Product 1

HCID 22273532HCID 22273532, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(2-Methoxyethoxy)ethanol (50 μl, 0.4 mmol) followed by diisopropyl azodicarboxylate (0.1 ml, 0.4 mmol) was added to a stirred solution of 4-(1,2-dimethylimidazol-5-yl)-2-{4-[N-(t-butoxycarbonyl)sulphamoyl]anilino}pyrimidine (Example 36; 90 mg, 0.2 mmol) and triphenylphosphine (105 mg, 0.4 mmol) in anhydrous THF (4 ml) under nitrogen at 0° C. The reaction was allowed to warm to ambient temperature and stirred for 1 hour. The mixture was poured directly on to an Isolute SCX-2 column, eluted first with MeOH (8×15 ml) and then the product was eluted with 2% methanolic ammonia (6×15 ml). The solvent was evaporated and the residue dissolved in EtOAc (25 ml), washed with saturated aqueous sodium hydrogen carbonate solution (2×25 ml), dried and the solvent evaporated to give the title compound (77 mg, 71%) as a yellow oil. NMR 1.38 (s, 9H), 2.49 (s, 3H), 3.38 (s, 3H), 3.56 (m, 2H), 3.68 (m, 2H), 3.76 (t, 2H), 3.96 (s, 3H), 4.06 (t, 2H), 7.03 (d, 1H), 7.49 (s, 1H), 7.58 (s, 1H), 7.78 (d, 2H), 7.93 (d, 2H), 8.40 (d, 1H); m/z 547.

Workup

  1. additionThe mixture was poured directly on to an Isolute SCX-2 column
  2. washeluted first with MeOH (8×15 ml)
  3. washthe product was eluted with 2% methanolic ammonia (6×15 ml)
  4. customThe solvent was evaporated
  5. dissolutionthe residue dissolved in EtOAc (25 ml)
  6. washwashed with saturated aqueous sodium hydrogen carbonate solution (2×25 ml)
  7. customdried
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-b2cecad687cb48fcb9fbeb48920a73cb
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

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