Dimethylformamide → HCID 45376751, compound

HRID 2195747Notes

Reaction equation

HRID 2195747 reaction equation
C(OC([N:8]1[C:16]2[CH:15]=[C:14]([C:17]3[O:18][C:19]([C:22]([OH:24])=O)=[CH:20][CH:21]=3)[N:13]=[CH:12][C:11]=2[CH:10]=[CH:9]1)=O)(C)(C)C.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2N=N1.C[CH2:48][N:49](C(C)C)C(C)C.[CH3:56][N:57]([CH:59]=[O:60])C>>[CH:33]1([C@H:48]([NH:49][C:22]([C:19]2[O:18][C:17]([C:14]3[N:13]=[CH:12][C:11]4[CH:10]=[CH:9][NH:8][C:16]=4[CH:15]=3)=[CH:21][CH:20]=2)=[O:24])[C:59](=[O:60])[NH:57][CH3:56])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 58492146HCID 58492146, compound

Product 1

HCID 45376751HCID 45376751, compoundYield 8%

Procedure

6-(5-Carboxy-furan-2-yl)-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (164 mg, 0.50 mmol) is dissolved in DMF (5 mL) and O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) (955 mg, 2.50 mmol), DIEA (0.55 mL, 3.00 mmol) is added as well as the amino acid (284 mg, 1.00 mmol). The reaction is capped and stirred at room temperature. After 5 hours, the reaction is quenched with water and extracted with EtOAc. The organic layer is washed with brine, dried over MgSO4, and the solvent is evaporated. The crude material is purified on reversed phase (HPLC). The product was obtained as a white solid 16 mg, 8%. LC/MS ESI m/z (M+H)+=381.70.

Workup

  1. customThe reaction is capped
  2. customthe reaction is quenched with water
  3. extractionextracted with EtOAc
  4. washThe organic layer is washed with brine
  5. dry with materialdried over MgSO4
  6. customthe solvent is evaporated
  7. customThe crude material is purified on reversed phase (HPLC)

Sources & evidence

ORD record
ord-4ea73d7bbd05480b9d875c8d77860ffe
Source dataset
uspto-grants-2012_12
Patent number
US08338367B2

Reaction notes

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