Hydrochloric Acid → HCID 25099654, compound

HRID 1809565Notes

Reaction equation

HRID 1809565 reaction equation
[ClH:1].Cl.Cl.[O:4]([C:11]1[C:12]([NH:27][C:28]2[S:32][N:31]=[C:30]([CH:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)[N:29]=2)=[N:13][CH:14]=[C:15]([S:17][C:18]2[CH:23]=[CH:22][N:21]=[C:20]3[CH:24]=[CH:25][S:26][C:19]=23)[CH:16]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(N(CC)CC)C.[C:46](OC(=O)C)(=[O:48])[CH3:47].C([O-])(O)=O.[Na+].Cl>C(Cl)Cl>[ClH:1].[ClH:1].[O:4]([C:11]1[C:12]([NH:27][C:28]2[S:32][N:31]=[C:30]([CH:33]3[CH2:38][CH2:37][N:36]([C:46](=[O:48])[CH3:47])[CH2:35][CH2:34]3)[N:29]=2)=[N:13][CH:14]=[C:15]([S:17][C:18]2[CH:23]=[CH:22][N:21]=[C:20]3[CH:24]=[CH:25][S:26][C:19]=23)[CH:16]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 67487241HCID 67487241, compound

Product 1

HCID 25099654HCID 25099654, compoundYield 147.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 250 mL flask was charged with 3-phenoxy-N-(3-(piperidin-4-yl)-1,2,4-thiadiazol-5-yl)-5-(thieno[3,2-b]pyridin-7-ylthio)pyridin-2-amine trihydrochloride (5.6 g, 8.92 mmol), triethylamine (9.94 mL, 71.3 mmol), and CH2Cl2 (100 mL). Acetic anhydride (1.26 mL, 13.4 mmol) was added and the reaction was stirred at ambient temperature for 10 minutes. The reaction was poured into saturated aqueous NaHCO3 and extracted with CH2Cl2. The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified on silica (5 to 10% methanol in EtOAc) to afford 1-(4-(5-(3-phenoxy-5-(thieno[3,2-b]pyridin-7-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-yl)ethanone dihydrochloride (4.16 g, 73.6% yield) as a yellow solid after HCl salt formation. 1H NMR (d6-DMSO) δ 12.48 (bs, 1H), 8.56 (d, 1H), 8.53 (d, 1H), 8.28 (d, 1H), 7.65 (d, 1H), 7.57 (d, 1H), 7.40 (m, 2H), 7.18 (m, 1H), 7.14 (m, 2H), 7.07 (d, 1H), 4.32 (m, 1H), 3.20 (m, 1H), 3.07 (m, 1H), 2.77 (m, 1H), 2.01 (m, 5H), 1.73 (m, 1H), 1.59 (m, 1H). Mass spectrum (apci) m/z=561.3 (M+H-2HCl).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on silica (5 to 10% methanol in EtOAc)

Sources & evidence

ORD record
ord-4e8d24b1f9244333bf1de5be0d75aa86
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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