Diisopropylethylamine → HCID 178504988, compound

HRID 1367890Notes

Reaction equation

[CH3:1][S:2]([NH:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[C:11]([C:16]([OH:18])=O)[N:12]=[CH:13]2)=[CH:8][CH:7]=1)(=[O:4])=[O:3].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.[NH:52]1[CH:56]=[CH:55][N:54]=[C:53]1[NH:57][C:58]([C:60]1[C:68]2[NH:67][C:66]([NH2:69])=[N:65][C:64]=2[CH:63]=[CH:62][CH:61]=1)=[O:59]>CN(C=O)C>[NH:54]1[CH:55]=[CH:56][N:52]=[C:53]1[NH:57][C:58]([C:60]1[C:68]2[NH:67][C:66]([NH:69][C:16]([C:11]3[N:12]=[CH:13][C:14]4[C:9]([CH:10]=3)=[CH:8][CH:7]=[C:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[CH:15]=4)=[O:18])=[N:65][C:64]=2[CH:63]=[CH:62][CH:61]=1)=[O:59]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 30 mg (0.11 mmol) of 7-methanesulfonylamino-isoquinoline-3-carboxylic acid in DMF (0.8 mL) was added 60 mg (0.15 mmol) of HBTU and DIEA (0.1 mL). The mixture was stirred for 10 min and then 24 mg (0.1 mmol) of 2-amino-3H-benzoimidazole-4-carboxylic acid (1H-imidazol-2-yl)-amide (intermediate B) was added. The reaction was heated at 80° C. for 1 h. After usual work up, the residue was purified by column chromatography eluting with DCM/methanol (v/v=10:1 to 8:1) to afford 5 mg (9%) of 7-methanesulfonylamino-isoquinoline-3-carboxylic acid [7-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amide. LCMS: 491 (M+1)+.

Workup

customAfter usual work up, the residue was purified by column chromatography
washeluting with DCM/methanol (v/v=10:1 to 8:1)

Sources & evidence

ORD record: ord-02dc98c6bc32402b8770f1415565b27b
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893267B2

Reaction notes

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