Water → HCID 18376081, compound

HRID 2117474Notes

Reaction equation

HRID 2117474 reaction equation
C([O:5][C:6](=[O:39])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]([S:30]([C:33]2[N:34]=[CH:35][N:36]([CH3:38])[CH:37]=2)(=[O:32])=[O:31])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[N:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[CH:20][CH:19]=2)[CH:10]=1)(C)(C)C.O.O1CCOCC1>Cl.C(OCC)C>[CH3:38][N:36]1[CH:37]=[C:33]([S:30]([N:16]([CH2:15][C:11]2[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=2)[O:8][CH2:7][C:6]([OH:39])=[O:5])[CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[N:25]=[CH:26][CH:27]=[CH:28][N:29]=3)=[CH:22][CH:23]=2)(=[O:31])=[O:32])[N:34]=[CH:35]1

Participants

6

Reactant 3

HCID 962WaterHCID 312751,4-DioxaneHCID 53899061HCID 53899061, compound

Product 1

HCID 18376081HCID 18376081, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

HCl. A solution of (3-(((1-methyl-1H-imidazole-4-sulfonyl)-(4-pyrimidin-2-yl-benzyl)-amino)-methyl)-phenoxy)-acetic acid tert-butyl ester prepared of Example 10, Step B (0.094 g, 0.17 mmol) in 1N HCl in diethyl ether was stirred for 20 minutes as a precipitate formed. To the mixture was added 1 mL water and 1 mL dioxane and the reaction was stirred for 3 hours. The solvent was removed in vacuo, azeotroping with ethanol to yield the title compound as a solid (54 mg). 1H NMR (400 MHz, CD3OD) δ 9.09 (m, 2H), 8.95 (bs, 1H), 8.24 (d, 2H), 8.04 (s, 1H), 7.71 (s, 1H), 7.44 (d, 2H), 7.13 (m, 1H), 6.82 (d, 1H), 6.76 (d, 1H), 6.69 (s, 1H), 4.61 (s, 2H), 4.54 (s, 2H), 4.46 (s, 2H), 3.92 (s, 3H); MS 494 (M+1).

Workup

  1. customformed
  2. stirringthe reaction was stirred for 3 hours
  3. customThe solvent was removed in vacuo
  4. customazeotroping with ethanol

Sources & evidence

ORD record
ord-742d268ed5744ed48627a245386729f1
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

Loading…