Diisopropylethylamine → Methyl [(3-{[(7-{3-[(3-methyl-2-furoyl)amino]phenoxy}thieno[3,2-b]pyridin-2-yl)carbonyl]amino}propyl)amino]acetate

HRID 525831Notes

Reaction equation

HRID 525831 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:26]=[CH:27][CH:28]=1)[O:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]2[CH:20]=[C:21]([C:23]([OH:25])=O)[S:22][C:15]=12)=[O:8].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.Cl.Cl.[NH2:73][CH2:74][CH2:75][CH2:76][NH:77][CH2:78][C:79]([O:81][CH3:82])=[O:80]>CN(C=O)C.C(OCC)(=O)C>[CH3:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:26]=[CH:27][CH:28]=1)[O:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]2[CH:20]=[C:21]([C:23]([NH:73][CH2:74][CH2:75][CH2:76][NH:77][CH2:78][C:79]([O:81][CH3:82])=[O:80])=[O:25])[S:22][C:15]=12)=[O:8]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 862903237-{3-[(3-Methyl-2-furoyl)amino]phenoxy}thieno[3,2-b]pyridine-2-carboxylic acidHCID 131735589Methyl [(3-aminopropyl)amino]acetate dihydrochloride

Product 1

HCID 86290414Methyl [(3-{[(7-{3-[(3-methyl-2-furoyl)amino]phenoxy}thieno[3,2-b]pyridin-2-yl)carbonyl]amino}propyl)amino]acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred, cooled (0° C.) solution of 7-{3-[(3-methyl-2-furoyl)amino]phenoxy}thieno[3,2-b]pyridine-2-carboxylic acid (150 mg, 0.38 mmol) in anhydrous DMF (10 ml) were added PyBOP (218 mg, 0.42 mmol) and N,N-diisopropylethylamine (245 mg, 1.9 mmol). The mixture was stirred at 0° C. for 10 minutes, followed by addition of methyl [(3-aminopropyl)amino]acetate dihydrochloride (100 mg, 0.46 mmol). Stirring was continued at 0° C. for another 40 minutes. The mixture was diluted with ethyl acetate (100 ml), washed with brine (4×100 ml), dried over Na2SO4, and concentrated to give the crude, which was purified by silica gel chromatography eluting with 5-8% methanol in chloroform to give methyl [(3-{[(7-{3-[(3-methyl-2-furoyl)amino]phenoxy}thieno[3,2-b]pyridin-2-yl)carbonyl]amino}propyl)amino]acetate as light beige solid. Yield: 98 mg, 49%.

Workup

  1. stirringStirring
  2. waitwas continued at 0° C. for another 40 minutes
  3. washwashed with brine (4×100 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give the crude, which
  7. customwas purified by silica gel chromatography
  8. washeluting with 5-8% methanol in chloroform

Sources & evidence

ORD record
ord-f82a363f57e24d4cb79de97226869860
Source dataset
uspto-grants-2016_05
Patent number
US09340555B2

Reaction notes

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