Diisopropylethylamine → HCID 58026684, compound
Reaction equation
[C:1]1([C:7]#[C:8][C:9]2[N:14]=[C:13]([C:15]([NH:17][C:18]3[NH:22][C:21]4[CH:23]=[CH:24][CH:25]=[C:26]([C:27](O)=[O:28])[C:20]=4[N:19]=3)=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.[CH3:64][S:65]([C:68]1[CH:75]=[CH:74][C:71]([CH2:72][NH2:73])=[CH:70][CH:69]=1)(=[O:67])=[O:66]>CN(C=O)C>[CH3:64][S:65]([C:68]1[CH:75]=[CH:74][C:71]([CH2:72][NH:73][C:27]([C:26]2[C:20]3[N:19]=[C:18]([NH:17][C:15]([C:13]4[CH:12]=[CH:11][CH:10]=[C:9]([C:8]#[C:7][C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)[N:14]=4)=[O:16])[NH:22][C:21]=3[CH:23]=[CH:24][CH:25]=2)=[O:28])=[CH:70][CH:69]=1)(=[O:66])=[O:67]Participants
6
Reactant 4
HCID 81531Diisopropylethylamine
HCID 27292694-Methylsulfonylbenzylamine hydrochloride
HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 669405682-[(6-Phenylethynyl-pyridine-2-carbonyl)-amino]-1H-benzoimidazole-4-carboxylic acidProduct 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 30 mg (0.07 mmol) of above 2-[(6-Phenylethynyl-pyridine-2-carbonyl)-amino]-1H-benzoimidazole-4-carboxylic acid in DMF (1 mL) was added 40 mg (0.1 mmol) of HBTU and DIEA (0.1 mL), the resulting mixture was stirred at room temperature for 10 min, then 40 mg (0.1 mmol) of 4-methanesulfonyl-benzylamine HCl salt was added. After usual work up as described in general procedure A, 21 mg (48%) of 2-[(6-phenylethynyl-pyridine-2-carbonyl)-amino]-1H-benzoimidazole-4-carboxylic acid 4-methanesulfonyl-benzylamide was obtained after column chromatography purification eluting with DCM/EtOAc (v/v from 5:1 to 1:1). LCMS: 550 (M+1)+.
Sources & evidence
- ORD record
- ord-e85f64c8d96743ec81b107105d49140f
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07893267B2
Reaction notes
Loading…