1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 24748566, compound

HRID 1887427Notes

Reaction equation

HRID 1887427 reaction equation
Br[CH2:2][CH:3]=[CH:4][C:5]([OH:7])=O.[CH:8]([NH:11][CH3:12])([CH3:10])[CH3:9].[Cl:13][C:14]1[CH:15]=[C:16]([NH:21][C:22]2[C:34]3[C:33]4[CH2:32][CH2:31][NH:30][CH2:29][C:28]=4[S:27][C:26]=3[N:25]=[CH:24][N:23]=2)[CH:17]=[CH:18][C:19]=1[Cl:20].CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:13][C:14]1[CH:15]=[C:16]([NH:21][C:22]2[C:34]3[C:33]4[CH2:32][CH2:31][N:30]([C:5](=[O:7])/[CH:4]=[CH:3]/[CH2:2][N:11]([CH:8]([CH3:10])[CH3:9])[CH3:12])[CH2:29][C:28]=4[S:27][C:26]=3[N:25]=[CH:24][N:23]=2)[CH:17]=[CH:18][C:19]=1[Cl:20]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 78485N-MethylisopropylamineHCID 81531DiisopropylethylamineHCID 841404-Bromo-2-butenoic acidHCID 58116912(3,4-Dichloro-phenyl)-(5,6,7,8-tetrahydro-9-thia-1,3,7-triaza-fluoren-4-yl)-amine

Product 1

HCID 24748566HCID 24748566, compoundYield 39.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-Bromo-but-2-enoic acid (638 mg, 3.87 mmol) in CH2Cl2 was added isopropylmethyamine (1.1 ml, 10.3 mmol), the mixture was stirred for 2 hours followed by addition of (3,4-dichloro-phenyl)-(5,6,7,8-tetrahydro-9-thia-1,3,7-triaza-fluoren-4-yl)-amine (1.0 g, 2.57 mmol), EDCI (493 mg, 2.58 mmol), DIPEA (1.8 ml, 10.3 mmol). The resulting mixture was stirred at RT overnight. Solvents were removed and residue was purified by HPLC to gave the desired compound (500 mg, 13%). 1H-NMR (DMSO-d6) δ 8.46 (m, 1H), 8.39 (s, 1H), 7.88 (m, 1H), 7.62 (m, 1H), 7.42 (t, 1H), 6.67 (m, 1H), 3.94 (m, 2H), 3.87 (m, 4H), 2.75 (m, 2H), 2.11 (s, 3H), 0.96 (d, 6H); LCMS RT=2.72 min, [M+1]+=490.3.

Workup

  1. stirringThe resulting mixture was stirred at RT overnight
  2. customSolvents were removed
  3. customresidue was purified by HPLC

Sources & evidence

ORD record
ord-4b7faaaed7e54eaea9d67fe82f15a2f6
Source dataset
uspto-grants-2013_08
Patent number
US08501755B2

Reaction notes

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