1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58116824, compound

HRID 38600

Reaction equation

HRID 38600 reaction equation
Br[CH2:2]/[CH:3]=[CH:4]/[C:5]([OH:7])=O.[CH3:8][N:9]([CH3:18])[C:10]([N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:11].CCN(C(C)C)C(C)C.[Cl:28][C:29]1[CH:30]=[C:31]([NH:36][C:37]2[C:38]3[C:45]4[CH2:46][CH2:47][NH:48][CH2:49][C:44]=4[S:43][C:39]=3[N:40]=[CH:41][N:42]=2)[CH:32]=[CH:33][C:34]=1[Cl:35].CCN=C=NCCCN(C)C>C(Cl)Cl.O>[Cl:28][C:29]1[CH:30]=[C:31]([NH:36][C:37]2[C:38]3[C:45]4[CH2:46][CH2:47][N:48]([C:5](=[O:7])/[CH:4]=[CH:3]/[CH2:2][N:15]5[CH2:14][CH2:13][N:12]([C:10]([N:9]([CH3:18])[CH3:8])=[O:11])[CH2:17][CH2:16]5)[CH2:49][C:44]=4[S:43][C:39]=3[N:40]=[CH:41][N:42]=2)[CH:32]=[CH:33][C:34]=1[Cl:35]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531Diisopropylethylamine2×HCID 712909n,n-Dimethylpiperazine-1-carboxamideHCID 64364114-Bromocrotonic acidHCID 58116912(3,4-Dichloro-phenyl)-(5,6,7,8-tetrahydro-9-thia-1,3,7-triaza-fluoren-4-yl)-amine

Product 1

HCID 58116824HCID 58116824, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

(2E)-4-Bromobut-2-enoic acid (106 mg, 0.64 mmol) and piperazine-1-carboxylic acid dimethylamide (107 mg, 0.68 mmol) were dissolved in DCM (5.0 mL), and DIPEA (111 mg, 0.85 mmol) was added. The mixture was stirred at rt for 2 h. Subsequently, the compound from Example 15A (150 mg, 0.43 mmol), DIPEA (55 mg, 0.43 mmol) and EDCI (82 mg, 0.43 mmol) were added. The reaction mixture was stirred at rt overnight. Then, water was added, and the mixture was extracted three times with DCM. The combined organic layers were dried over sodium sulfate. The solvent was removed in vacuo, and the residue was purified by preparative HPLC to yield 59 mg (24%) of the title compound.

Workup

  1. stirringThe reaction mixture was stirred at rt overnight
  2. extractionthe mixture was extracted three times with DCM
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-3db0a56a8e02415888246276a89874c5
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Linked notes

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