Acetic Acid → 2-phenyl-5-(3-(pyrrolidin-1-yl)propyl)-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide

HRID 1799134Notes

Reaction equation

HRID 1799134 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.O=[CH:7][CH2:8][CH2:9][C:10]1[S:14][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:12][C:11]=1[C:21]([NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]1[S:31][C:32]2[C:37]([N:38]=1)=[CH:36][CH:35]=[CH:34][N:33]=2)=[O:22].CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClC(Cl)C>[C:15]1([C:13]2[S:14][C:10]([CH2:9][CH2:8][CH2:7][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[C:11]([C:21]([NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]3[S:31][C:32]4[C:37]([N:38]=3)=[CH:36][CH:35]=[CH:34][N:33]=4)=[O:22])[N:12]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 585518735-(3-oxopropyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide

Product 1

HCID 462451312-phenyl-5-(3-(pyrrolidin-1-yl)propyl)-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamideYield 31.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Pyrrolidine (88 μL, 1.06 mmol) was added to a solution of 5-(3-oxopropyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide (250 mg, 0.53 mmol) and AcOH (127 mg, 2.1 mmol) in dichloroethane (DCE) (10 mL). The reaction mixture was stirred for 1 h. Sodium triacetoxyborohydride (449 mg, 2.1 mmol) was added and stirring continued for 16 h. The reaction mixture was poured into sat aq NaHCO3 and extracted with DCM. The combined organics were washed with brine, dried (MgSO4), and concentrated. The crude product was purified by MPLC eluting with CH2Cl2/MeOH+1% TEA(0-10% gradient) to give the title compound (87 mg, 31% yield). MS Calcd for C29H27N5OS2: 525.17. Found (M+H)+ m/z=526.

Workup

  1. stirringstirring
  2. waitcontinued for 16 h
  3. additionThe reaction mixture was poured
  4. extractionextracted with DCM
  5. washThe combined organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe crude product was purified by MPLC
  9. washeluting with CH2Cl2/MeOH+1% TEA(0-10% gradient)

Sources & evidence

ORD record
ord-7a08fc50ab9644a1aa16137364d25e73
Source dataset
uspto-grants-2013_01
Patent number
US08343997B2

Reaction notes

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