Sodium Carbonate → HCID 67347539, compound

HRID 1676280Notes

Reaction equation

HRID 1676280 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[NH2:8][C:9]1[CH:32]=[CH:31][C:12]([O:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]3[CH:20]=[C:21]([C:23]4[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=4)[S:22][C:15]=23)=[C:11]([F:33])[CH:10]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[F:33][C:11]1[CH:10]=[C:9]([CH:32]=[CH:31][C:12]=1[O:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]2[CH:20]=[C:21]([C:23]3[CH:30]=[CH:29][C:26]([CH2:27][N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)=[CH:25][CH:24]=3)[S:22][C:15]=12)[NH2:8]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 86614647HCID 86614647, compound

Product 1

HCID 67347539HCID 67347539, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 20 mL vial was charged with 1-methylpiperazine (0.0457 mL, 0.412 mmol), 4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)benzaldehyde (Example 94, Step A; 0.150 g, 0.329 mmol) and CH2Cl2 (5 mL). The reaction mixture was stirred for 30 minutes and sodium triacetoxyborohydride (0.0977 g, 0.461 mmol) was added slowly over five minutes, and then the reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into Na2CO3 (100 mL) and extracted with CH2Cl2 (2×100 mL). The organic layers were over sodium sulfate, filtered and concentrated to provide the product (103 mg, 64%) as a brown solid. LRMS (APCI+) 449 (M+1H).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 4 hours
  2. extractionextracted with CH2Cl2 (2×100 mL)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b18e614ced6449ec97c61ddb91dfbf23
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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