1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68492418, compound

HRID 444722Notes

Reaction equation

HRID 444722 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:11]([OH:13])=O)[CH:5]=[CH:6][C:7]=1[F:8].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:42][CH2:43][C:44]1[CH:59]=[CH:58][C:47]([C:48]([NH:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=2[NH2:57])=[O:49])=[CH:46][CH:45]=1>CN(C=O)C>[NH2:57][C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][C:51]=1[NH:50][C:48](=[O:49])[C:47]1[CH:46]=[CH:45][C:44]([CH2:43][NH:42][C:11](=[O:13])[C:10]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:9][C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=2)=[CH:59][CH:58]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 588172504-(Aminomethyl)-N-(2-aminophenyl)benzamideHCID 68491438HCID 68491438, compound

Product 1

HCID 68492418HCID 68492418, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(3,4-difluorophenyl)-2-(4-fluorophenyl)acrylic acid (0.5 g, 1.7 mmol) in DMF (5 mL) was added TEA (0.75 mL, 5.4 mmol), EDCI (0.68 g, 3.5 mmol), HOBt (0.25 g, 1.8 mmol) followed by the 4-(aminomethyl)-N-(2-aminophenyl)benzamide (0.52 g, 1.9 mmol). The reaction mixture was stirred at room temperature for 12 hours. Subsequently it was concentrated under reduced pressure to half the volume and the resulted solution was poured into water. Upon standing a white precipitate formed, was filtered, washed with water followed by ether gave the pure product (0.3 g, 30% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 4.41 (2H, d, CH2), 4.88 (2H, s, NH2), 6.59 (1H, t, Ar—H), 6.77 (1H, d, Ar—H), 6.88 (1H, s, Ar—H), 6.96 (2H, m, Ar—H), 7.16 (1H, d, Ar—H), 7.24-7.38 (7H, m, Ar—H), 7.47 (1H, s, ═CH), 7.92 (2H, d, Ar—H), 8.14 (1H, t, NH), 9.61 (1H, s, NH). MS m/z: 502.1 (M++1).

Workup

  1. concentrationSubsequently it was concentrated under reduced pressure to half the volume
  2. additionthe resulted solution was poured into water
  3. customformed
  4. filtrationwas filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-542e93ce883449bba17824d54278057c
Source dataset
uspto-grants-2013_07
Patent number
US08476255B2

Reaction notes

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