2-Thiophenecarboxaldehyde → HCID 68818603, compound

HRID 1785314Notes

Reaction equation

HRID 1785314 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[C:11]([Br:12])=[CH:10][N:9]=[C:8]([NH:13][C:14]2[CH:15]=[C:16]([NH:20][C:21]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:22])[CH:17]=[CH:18][CH:19]=2)[N:7]=1.[S:28]1[CH:32]=[CH:31][CH:30]=[C:29]1C=O.[CH2:35](N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[Br:12][C:11]1[C:6]([NH:5][CH2:4][CH2:3][CH2:2][NH:1][CH2:35][C:30]2[CH:31]=[CH:32][S:28][CH:29]=2)=[N:7][C:8]([NH:13][C:14]2[CH:15]=[C:16]([NH:20][C:21]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:22])[CH:17]=[CH:18][CH:19]=2)=[N:9][CH:10]=1

Participants

6

Reactant 4

HCID 73642-ThiophenecarboxaldehydeHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 57593297HCID 57593297, compound

Product 1

HCID 68818603HCID 68818603, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(3-((4-((3-aminopropyl)amino)-5-bromo-2-pyrimidinyl)amino)phenyl)-1-pyrrolidinecarboxamide (1.0 g, 1.97 mmol) in THF (30 mL) was added 2-thiophenecarboxaldehyde (184 mg, 1.64 mmol, 0.8 equiv.), triethylamine (362 mg, 3-6 mmol, 1.8 equiv.) and sodium triacetoxyborohydride (688 mg, 3.25 mmol, 1.6 equiv.). The resulting mixture was stirred overnight at room temperature under N2. The reaction was quenched by satuarated sodium bicarbonate (30 mL) and was extracted with ethyl acetate (3×30 mL). The reaction mixture was concentrated. Purification by HPLC chromatography using acetonitrile/water gave the title compound (310 mg).

Workup

  1. customThe reaction was quenched by satuarated sodium bicarbonate (30 mL)
  2. extractionwas extracted with ethyl acetate (3×30 mL)
  3. concentrationThe reaction mixture was concentrated
  4. customPurification by HPLC chromatography

Sources & evidence

ORD record
ord-58bee59f13cb4b3ea42a1a24ff3ce534
Source dataset
uspto-grants-2009_03
Patent number
US07504410B2

Reaction notes

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