Dibutylamine → HCID 11774509, compound

HRID 2103775Notes

Reaction equation

HRID 2103775 reaction equation
[C:1]([C:9]1[O:10][C:11]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:12]=2[C:13]=1[CH2:14][C:15]([OH:17])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.[CH2:34]([NH:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:35][CH2:36][CH3:37].CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)CCl>[C:1]([C:9]1[O:10][C:11]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:12]=2[C:13]=1[CH2:14][C:15]([N:38]([CH2:39][CH2:40][CH2:41][CH3:42])[CH2:34][CH2:35][CH2:36][CH3:37])=[O:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8148DibutylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 68950368HCID 68950368, compound

Product 1

HCID 11774509HCID 11774509, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 10.6 mg (2-benzoyl-5-methoxy-1-benzofuran-3-yl)acetic acid from the Step B above, 7.8 mg HOBt and 13.1 mg EDC were added 6.6 mg dibutylamine and 0.5 mL DMF followed by 21 μL DIEA. After stirring at room temperature over night, it was heated in a 55° C. oil bath for 8 hours. It was purified directly on RP-HPLC using 60-95% MeCN gradient. The fractions containing pure product were pooled and lyophilized to give the title compound. 1H NMR (CDCl3, 500 MHz) 8.10˜8.13 (m, 2H), 7.62˜7.66 (m, 1H), 7.53˜7.57 (m, 2H), 7.45 (d, J=8.9 Hz, 1H), 7.275 (d, J=2.7 Hz, 1H), 7.14 (dd, J=2.7 & 9.1 Hz, 1H), 4.39 (s, 2H), 3.89 (s, 3H), 3.43˜3.47 (m, 2H), 3.37˜3.40 (m, 2H), 1.51˜1.61 (m, 4H), 1.26˜1.38 (m, 4H), 0.94 (t, J=7.3 Hz, 3H), 0.90 (t, J=7.3 Hz, 3H). LC-MS: 4.24 min. (m/Z=422.3, 444.3).

Workup

  1. temperatureit was heated in a 55° C. oil bath for 8 hours
  2. customIt was purified directly on RP-HPLC using 60-95% MeCN gradient
  3. additionThe fractions containing pure product

Sources & evidence

ORD record
ord-2a4ce9c2b52447daae7f8597956f6c9d
Source dataset
uspto-grants-2009_08
Patent number
US07576122B2

Reaction notes

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