Diisopropylethylamine → HCID 58026684, compound

HRID 1845036Notes

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

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-fbb70a1500254ee886295c31beeb12ed
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946259B2

Reaction notes

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Reaction equation

Participants

Reactant 4

Product 1

Reagents, catalysts & solvents 1

Procedure

Sources & evidence

Reaction notes