1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58116979, compound
Reaction equation
Br[CH2:2]/[CH:3]=[CH:4]/[C:5]([OH:7])=O.Cl.[O:9]1[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.CCN(C(C)C)C(C)C.[Cl:25][C:26]1[CH:27]=[C:28]([NH:33][C:34]2[C:39]([C:40]#[N:41])=[CH:38][N:37]=[C:36]3[S:42][C:43]4[CH2:44][NH:45][CH2:46][CH2:47][C:48]=4[C:35]=23)[CH:29]=[CH:30][C:31]=1[Cl:32].CCN=C=NCCCN(C)C>C(Cl)Cl.O>[Cl:25][C:26]1[CH:27]=[C:28]([NH:33][C:34]2[C:39]([C:40]#[N:41])=[CH:38][N:37]=[C:36]3[S:42][C:43]4[CH2:44][N:45]([C:5](=[O:7])/[CH:4]=[CH:3]/[CH2:2][N:12]5[CH2:13][CH2:14][CH2:15][O:9][CH2:10][CH2:11]5)[CH2:46][CH2:47][C:48]=4[C:35]=23)[CH:29]=[CH:30][C:31]=1[Cl:32]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
(2E)-4-Bromobut-2-enoic acid (53 mg, 0.32 mmol) and 1,4-oxazepane hydrochloride (48 mg, 0.34 mmol) were dissolved in DCM (2.0 mL), and DIPEA (96 mg, 0.75 mmol) was added. The mixture was stirred at rt for 2 h. Subsequently, 4-[(3,4-dichlorophenyl)amino]-5,6,7,8-tetrahydrothieno[2,3-b:5,4-c′]dipyridine-3-carbonitrile from Example 88A (80 mg, 0.21 mmol), DIPEA (28 mg, 0.21 mmol) and EDCI (41 mg, 0.21 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 19 mg (16%) of the title compound.
Workup
- stirringThe reaction mixture was stirred at rt overnight
- extractionthe mixture was extracted three times with DCM
- dry with materialThe combined organic layers were dried over sodium sulfate
- customThe solvent was removed in vacuo
- customthe residue was purified by preparative HPLC
Sources & evidence
- ORD record
- ord-af6f3ce295f94e72a2ba6f065a48220a
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08524722B2
Reaction notes
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