Acetic Anhydride → Amg-517

HRID 857642Notes

Reaction equation

HRID 857642 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](OC(=O)C)(=[O:30])[CH3:29]>>[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:28](=[O:30])[CH3:29])[S:24][C:20]=4[CH:19]=[CH:18][CH:17]=3)[CH:10]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 100916504-[6-(4-Trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzothiazol-2-ylamine

Product 1

HCID 16007367Amg-517

Conditions

Temperature
105 °C

Procedure

A mixture of 4-[6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]benzothiazol-2-ylamine, (Example 65), (97 mg, 0.25 mmol) and acetic anhydride (0.24 mL, 2.5 mmol) was heated in a 105° C. oil bath for 8 h. The solvent was evaporated and the solid that formed was recrystallized from EtOAc/hexanes, and dried under vacuum to give the title compound. MS (ESI, pos. ion) m/z: 431 (M+1). Mp: 219.0–220.5° C. Anal. Calcd for C20H13F3N4O2S.0.75 H2O: C, 54.11; H, 3.29; N, 12.62; S, 7.22. Found: C, 54.12; H, 3.07; N, 12.61; S, 7.30.

Workup

  1. customThe solvent was evaporated
  2. customthe solid that formed
  3. customwas recrystallized from EtOAc/hexanes
  4. customdried under vacuum

Sources & evidence

ORD record
ord-5403d380ca82482d8ebd6ee91bff3f03
Source dataset
uspto-grants-2006_12
Patent number
US07144888B2

Reaction notes

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