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Acetic Anhydride → 1-(4-((2-(3-Phenoxy-5-(thieno[3,2-b]pyridin-7-ylthio)pyridin-2-ylamino)thiazol-4-yl)methyl)piperidin-1-yl)ethanone

HRID 1806191
Notes
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Reaction equation

HRID 1806191 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].Cl.Cl.[O:10]([C:17]1[C:18]([NH:33][C:34]2[S:35][CH:36]=[C:37]([CH2:39][CH:40]3[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]3)[N:38]=2)=[N:19][CH:20]=[C:21]([S:23][C:24]2[CH:29]=[CH:28][N:27]=[C:26]3[CH:30]=[CH:31][S:32][C:25]=23)[CH:22]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C1COCC1>[O:10]([C:17]1[C:18]([NH:33][C:34]2[S:35][CH:36]=[C:37]([CH2:39][CH:40]3[CH2:45][CH2:44][N:43]([C:1](=[O:3])[CH3:2])[CH2:42][CH2:41]3)[N:38]=2)=[N:19][CH:20]=[C:21]([S:23][C:24]2[CH:29]=[CH:28][N:27]=[C:26]3[CH:30]=[CH:31][S:32][C:25]=23)[CH:22]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 866315353-phenoxy-N-(4-(piperidin-4-ylmethyl)thiazol-2-yl)-5-(thieno[3,2-b]pyridin-7-ylthio)pyridin-2-amine dihydrochloride

Product 1

HCID 577429321-(4-((2-(3-Phenoxy-5-(thieno[3,2-b]pyridin-7-ylthio)pyridin-2-ylamino)thiazol-4-yl)methyl)piperidin-1-yl)ethanoneYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

Added acetic anhydride (0.0169 g, 0.165 mmol) to a mixture of 3-phenoxy-N-(4-(piperidin-4-ylmethyl)thiazol-2-yl)-5-(thieno[3,2-b]pyridin-7-ylthio)pyridin-2-amine dihydrochloride (0.100 g, 0.165 mmol), triethylamine (0.0837 g, 0.827 mmol), and THF (5 mL) at 0° C. Warmed to ambient temperature and stirred for 4 hours. Partitioned between ethyl acetate and 2N NaOH, washed with water, brine, dried, and concentrated. The residue was dissolved in dichloromethane (2 mL) and 1N HCl in ether was added. Diluted in hexanes, and concentrated, added hexanes again and concentrated to afford the title compound ((Mixture of rotamers; 0.092 g, 91.2% yield) as a light yellow powder: 1H NMR (d6-DMSO) δ 8.65 (d, 1H); 8.47 (d, 1H), 8.46 (s, 1H), 7.77 (d, 1H), 7.41 (s, 1H), 7.41 (d, 2H), 7.15-7.20 (m, 4H), 6.84 (s, 1H), 0.95-4.36 (m, 11H), 1.97 (s, 3H).

Workup

  1. customPartitioned between ethyl acetate and 2N NaOH
  2. washwashed with water, brine
  3. customdried
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in dichloromethane (2 mL)
  6. addition1N HCl in ether was added
  7. additionDiluted in hexanes
  8. concentrationconcentrated
  9. additionadded hexanes again
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-f1ae9ada1f424f68bf569fc46e3669b0
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08354540B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes