Dimethylformamide → HCID 20746071, compound

HRID 2308102Notes

Reaction equation

HRID 2308102 reaction equation
[CH3:1]N(C=O)C.[CH3:6][C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([O:16][C:17]1[CH:22]=[CH:21][N:20]=[C:19]3[CH:23]=[C:24]([C:26]([OH:28])=[O:27])[S:25][C:18]=13)=[CH:11][CH:10]=2.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CCOC(C)=O.CO>[CH3:1][O:27][C:26]([C:24]1[S:25][C:18]2[C:19](=[N:20][CH:21]=[CH:22][C:17]=2[O:16][C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7]([CH3:6])=[CH:15]3)[CH:23]=1)=[O:28]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22603695HCID 22603695, compound

Product 1

HCID 20746071HCID 20746071, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of DMF was added 7-(2-Methyl-1H-indol-5-yloxy)-thieno[3,2-b]pyridine-2-carboxylic acid (0.6 g, 1.85 mmol), DIEA (0.62 mL, 3.70 mmol), HATU (0.77 g, 2.03) and MeOH (0.5 mL). The solution was stirred for 3 h then 50 mL of EtOAc added and partitioned between 50/50 NaHCO3 (2×50 mL). The organic layer was dried over Na2SO4 then concentrated. Purification was through silica (50 mL) eluting with EtOAc/Hex (2:1). The purified fraction combined and concentrated to give 7-(2-Methyl-1H-indol-5-yloxy)-thieno[3,2-b]pyridine-2-carboxylic acid methyl ester as white foam (0.6 g, 96%). HPLC: Rt 4.01 min. (100% area). 1H NMR (CDCl3-d3, 400 MHz) δ: 8.42 (1H, d, J=5.6 Hz), 8.29 (1H, bs), 7.26-7.23 (2H, m), 6.85 (1H, dd, J=7.5, 1.6 Hz), 6.51 (1H, d, J=5.3 Hz), 6.17 (1H, s), 3.91 (3H, s), 2.40 (3H, s). LCMS (ACPI) M+H+ m/z: 339.1.

Workup

  1. custompartitioned between 50/50 NaHCO3 (2×50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationthen concentrated
  4. customPurification
  5. washeluting with EtOAc/Hex (2:1)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-11a3381f41724b799309f5cf1fff98f3
Source dataset
uspto-grants-2004_12
Patent number
US06833456B2

Reaction notes

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