Diisopropylethylamine → 2-(benzyloxy)-N-(3-fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenyl)acetamide

HRID 1676276Notes

Reaction equation

HRID 1676276 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[CH:16]=[CH:17][S:18][C:11]=12)[NH2:5].C(N(C(C)C)CC)(C)C.[CH2:28]([O:35][CH2:36][C:37](Cl)=[O:38])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)Cl>[CH2:28]([O:35][CH2:36][C:37]([NH:5][C:4]1[CH:6]=[CH:7][C:8]([O:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]3[CH:16]=[CH:17][S:18][C:11]=23)=[C:2]([F:1])[CH:3]=1)=[O:38])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 177085Benzyloxyacetyl chlorideHCID 594244303-Fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)aniline

Product 1

HCID 589495052-(benzyloxy)-N-(3-fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3-fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)aniline (Example 1-B; 67 mg, 0.258 mmol) in 1 mL CH2Cl2 at room temperature under nitrogen was added diisopropylethylamine (68 μL, 0.387 mmol) followed by 2-(benzyloxy)acetyl chloride (41 μL, 0.258 mmol). After 1 hour, the reaction was diluted to 30 mL with CH2Cl2 and washed 2×30 mL with 10% citric acid and 2×30 mL with saturated NaHCO3. The organics were isolated, dried (MgSO4), filtered and concentrated. The crude product was loaded onto a Biotage 12S column with 2/3 EtOAc/hexanes and eluted. The fractions containing the product were pooled and concentrated to a yellow oil (68 mg, 64%). 1H NMR (400 MHz, CDCl3) δ 8.51 (d, 1H), 8.44 (br s, 1H), 7.74 (d, 1H), 7.57 (d, 1H), 7.39 (m, 5H), 7.24 (m, 3H), 6.50 (d, 1H), 4.68 (s, 2H), 4.13 (s, 2H). LRMS (ESI pos) m/e 409.0 (M+1).

Workup

  1. washwashed 2×30 mL with 10% citric acid and 2×30 mL with saturated NaHCO3
  2. customThe organics were isolated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washeluted
  7. additionThe fractions containing the product
  8. concentrationconcentrated to a yellow oil (68 mg, 64%)

Sources & evidence

ORD record
ord-0e4d1171085e4069a214e052f474ef70
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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