Acetic Anhydride → HCID 59287309, compound

HRID 1972177Notes

Reaction equation

HRID 1972177 reaction equation
Cl.Cl.[CH3:3][C:4]1[C:9]([O:10][C:11]2[C:16]([S:17][C:18]3[CH:23]=[CH:22][N:21]=[C:20]4[CH:24]=[CH:25][S:26][C:19]=34)=[CH:15][N:14]=[C:13]([NH:27][C:28]3[S:29][CH:30]=[C:31]([CH:33]4[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]4)[N:32]=3)[CH:12]=2)=[CH:8][CH:7]=[CH:6][N:5]=1.C(N(CC)CC)C.[C:46](OC(=O)C)(=[O:48])[CH3:47].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:3][C:4]1[C:9]([O:10][C:11]2[C:16]([S:17][C:18]3[CH:23]=[CH:22][N:21]=[C:20]4[CH:24]=[CH:25][S:26][C:19]=34)=[CH:15][N:14]=[C:13]([NH:27][C:28]3[S:29][CH:30]=[C:31]([CH:33]4[CH2:38][CH2:37][N:36]([C:46](=[O:48])[CH3:47])[CH2:35][CH2:34]4)[N:32]=3)[CH:12]=2)=[CH:8][CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 86640991HCID 86640991, compound

Product 1

HCID 59287309HCID 59287309, compoundYield 110.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(2-Methylpyridin-3-yloxy)-N-(4-(piperidin-4-yl)thiazol-2-yl)-5-(thieno[3,2-b]pyridin-7-ylthio)pyridin-2-amine dihydrochloride (0.051 g, 0.08 mmol) was dissolved in dichloromethane (2 mL). Triethylamine (0.10 mL, 0.74 mmol) and acetic anhydride (0.017 mL, 0.19 mmol) were added and the reaction was stirred at ambient temperature overnight. Saturated sodium bicarbonate solution was added, and the reaction was extracted with ethyl acetate. The organic layer was dried and concentrated to give the title compound (0.051 g, 70% yield) as yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.50 (d, 1H), 8.41 (dd, 1H), 7.73 (d, 1H), 7.56 (d, 1H), 7.19 (m, 1H), 7.17 (m, 1H), 6.92 (d, 1H), 6.40 (d, 1H), 6.36 (s, 1H), 4.67 (m, 1H), 3.86 (m, 1H), 3.13 (m, 1H), 2.69 (m, 2H), 2.16 (s, 3H), 1.94 (m, 2H), 1.60 (m, 2H).

Workup

  1. extractionthe reaction was extracted with ethyl acetate
  2. customThe organic layer was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ff81d758251f4d82a82616e3411deefc
Source dataset
uspto-grants-2013_04
Patent number
US08431713B2

Reaction notes

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