Triethylamine → HCID 58759722, compound

HRID 857646Notes

Reaction equation

HRID 857646 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][N:12]=[C:11]([O:15][C:16]3[C:21]4[N:22]=[C:23]([NH2:25])[S:24][C:20]=4[CH:19]=[CH:18][CH:17]=3)[CH:10]=2)=[CH:5][CH:4]=1.[C:28]([O:31][C:32](=O)[CH:33](C1C=CC=CC=1)[OH:34])(=[O:30])[CH3:29].C(N(CC)CC)C>O1CCOCC1>[F:27][C:2]([F:26])([F:1])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][N:12]=[C:11]([O:15][C:16]3[C:21]4[N:22]=[C:23]([NH:25][C:33]([CH2:32][O:31][C:28](=[O:30])[CH3:29])=[O:34])[S:24][C:20]=4[CH:19]=[CH:18][CH:17]=3)[CH:10]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 100916504-[6-(4-Trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzothiazol-2-ylamineHCID 20537972Acetic hydroxy(phenyl)acetic anhydride

Product 1

HCID 58759722HCID 58759722, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

This material was prepared according to the procedure described in Example 78(a) using 4-[6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzothiazol-2-ylamine, (Example 65), (0.36 g, 0.9 mmol), O-acetyl mandelic acid (0.41 mL, 1.8 mmol, Heico Chemicals, Inc.) and triethylamine (0.25 mL, 1.8 mmol) in dioxane (3 mL). Purification by silica gel chromatography (3:1 hexanes: EtOAc) provided the title compound as a light-yellow foam. MS (ESI, pos. ion) m/z: 565 (M+1). Mp: 118.6–138.4° C.

Workup

  1. customThis material was prepared
  2. customPurification by silica gel chromatography (3:1 hexanes: EtOAc)

Sources & evidence

ORD record
ord-fb34d1cc3c194ae494393d244566f5a1
Source dataset
uspto-grants-2006_12
Patent number
US07144888B2

Reaction notes

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