Diisopropylethylamine → HCID 178504988, compound

HRID 1910161Notes

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-b170b5f55ada417ebe89c7990510a682
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598353B2

Reaction notes

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