2-Furancarboxylic acid → HCID 16722974, compound

HRID 555262Notes

Reaction equation

HRID 555262 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.FC(F)(F)C(O)=O.[NH2:37][CH2:38][CH2:39][N:40]1[C:44]2[CH:45]=[CH:46][C:47]([C:49]([N:51]3[CH2:57][C:56]4([CH3:59])[CH2:58][CH:52]3[CH2:53][C:54]([CH3:61])([CH3:60])[CH2:55]4)=[O:50])=[CH:48][C:43]=2[N:42]=[CH:41]1>C1COCC1>[CH3:59][C:56]12[CH2:58][CH:52]([N:51]([C:49]([C:47]3[CH:46]=[CH:45][C:44]4[N:40]([CH2:39][CH2:38][NH:37][C:6]([C:2]5[O:1][CH:5]=[CH:4][CH:3]=5)=[O:8])[CH:41]=[N:42][C:43]=4[CH:48]=3)=[O:50])[CH2:57]1)[CH2:53][C:54]([CH3:61])([CH3:60])[CH2:55]2

Participants

6

Reactant 4

HCID 69192-Furancarboxylic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 66987502HCID 66987502, compound

Product 1

HCID 16722974HCID 16722974, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-furoic acid (37 mg, 0.33 mmol) in dry THF (2 mL) at room temperature under an inert atmosphere of nitrogen were added HOBt (49 mg, 0.36 mmol) and EDAC (82 mg, 0.43 mmol), and the resulting solution was stirred for 30 min. [1-(2-Aminoethyl)-1H-benzoimidazol-5-yl]-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-methanone trifluoroacetate (150 mg, 0.33 mmol) was added to the solution followed by TEA (0.184 mL, 1.32 mmol), and the reaction mixture was stirred for 16 h at room temperature. The volatiles were evaporated in vacuo and the resulting solid was purified by preparative HPLC, dried in vacuo at 50° C. affording 100 mg (70%) of the title compound as a solid. MS-ESI m/z 435; 1H NMR (400 MHz, DMSO-d6) δ 0.88-0.99 (m, 6H), 1.07 (d, 3H), 1.29-1.41 (m, 4H), 1.50-1.52 (m) and 2.10-2.11 (m, 1H), 1.76-1.79 (m, 1H), 3.02 (d), 3.13 (d), 3.32 (d) and 3.47 (d, 2H), 3.69 (t, 2H), 3.87-3.89 (m) and 4.39-4.41 (m, 1H), 4.56 (t, 2H), 6.58 (s, 1H), 6.98 (d, 1H), 7.48 (dd, 1H), 7.77-7.82 (m, 2H), 7.89 (t, 1H), 8.54-8.58 (m, 1H), 9.07 (d, 1H).

Workup

  1. additionwas added to the solution
  2. customThe volatiles were evaporated in vacuo
  3. customthe resulting solid was purified by preparative HPLC
  4. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-69c51bf2f20b48dc8ccd508b4c6bd561
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

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