5-Nitro-2-Furoic Acid → 1-(9H-carbazol-4-yloxy)-3-{[1-(5-nitro-2-furoyl)piperidin-4-yl]amino}propan-2-ol

HRID 507339

Reaction equation

HRID 507339 reaction equation
[N+:1]([C:4]1[O:8][C:7]([C:9]([OH:11])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH:33]1[C:45]2[NH:44][C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:37]=2[C:36]([O:46][CH2:47][CH:48]([OH:57])[CH2:49][NH:50][CH:51]2[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]2)=[CH:35][CH:34]=1>CN(C=O)C.C(Cl)Cl>[CH:33]1[C:45]2[NH:44][C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:37]=2[C:36]([O:46][CH2:47][CH:48]([OH:57])[CH2:49][NH:50][CH:51]2[CH2:52][CH2:53][N:54]([C:9]([C:7]3[O:8][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)=[O:11])[CH2:55][CH2:56]2)=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 125775-Nitro-2-Furoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 588781181-(9H-carbazol-4-yloxy)-3-(piperidin-4-ylamino)propan-2-ol

Product 1

HCID 167312171-(9H-carbazol-4-yloxy)-3-{[1-(5-nitro-2-furoyl)piperidin-4-yl]amino}propan-2-olYield 32%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-Nitrofuroic acid (0.14 g, 0.88 mmol) in DMF (6 mL) was added TEA (0.17 mL, 1.2 mmol), EDCI (0.2 g, 1.0 mmol), HOBt (0.031 g, 0.23 mmol), followed by 1-(9H-carbazol-4-yloxy)-3-(piperidin-4-ylamino)propan-2-ol (0.2 g, 0.6 mmol, prepared by following the procedure described in step 11, example 64). The reaction was stirred at room temperature for 12 hours and was diluted with DCM (25 mL), washed with water and brine solution. The organic layer was dried over anhydrous Na2SO4, concentrated and purified by silica gel column chromatography using DCM/MeOH (9.5:0.5) to afford the title compound as red colored paste (45 mg, 32% yield). 1H NMR (400 MHz, DMSO): δ 1.20-1.80 (m, 3H), 1.90-2.30 (m, 2H), 2.50-3.60 (m, 6H), 4.00-4.60 (m, 3H), 6.72 (d, 1H, J=8.0 Hz), 6.90-7.60 (m, 6H), 7.77 (d, 1H, J=3.6 Hz), 8.22 (d, 1H, J=8.0 Hz), and 11.30 (s, 1H). MS m/z: 478.1 (M+).

Workup

  1. customprepared
  2. washwashed with water and brine solution
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-0eb2234be5104da5a65f085d2f234fac
Source dataset
uspto-grants-2010_08
Patent number
US07786142B2

Linked notes

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