Diisopropylethylamine → HCID 58026472, compound

HRID 1367945Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([C:25]([OH:27])=O)[C:6]2[N:10]=[C:9]([NH:11][C:12]([C:14]3[N:15]=[CH:16][C:17]4[C:22]([CH:23]=3)=[CH:21][CH:20]=[CH:19][CH:18]=4)=[O:13])[NH:8][C:7]=2[CH:24]=1)#[N:2].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.S(O)(O)(=O)=O.[NH2:66][C:67]1[NH:68][CH:69]=[CH:70][N:71]=1>O.CN(C=O)C>[C:1]([C:3]1[CH:4]=[C:5]([C:25](=[O:27])[NH:66][C:67]2[NH:68][CH:69]=[CH:70][N:71]=2)[C:6]2[N:10]=[C:9]([NH:11][C:12]([C:14]3[N:15]=[CH:16][C:17]4[C:22]([CH:23]=3)=[CH:21][CH:20]=[CH:19][CH:18]=4)=[O:13])[NH:8][C:7]=2[CH:24]=1)#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

0.20 g (0.56 mmol) of 6-cyano-2-[(isoquinoline-3-carbonyl)-amino]-1H-benzoimidazole-4-carboxylic acid and 0.21 g (0.56 mmol) of HBTU were combined in a flask charged with 3 mL of DMF and 1 mL of DIEA. This reaction mixture was then treated with 0.07 g (0.56 mmol) of 2-amino-imidazole sulfate and stirred at 80° C. for 1 h. The reaction mixture was diluted with water, and the resultant solid precipitate was filtered and washed with saturated NaHCO3. The solid was dissolved with MeOH, evaporated onto silica gel and isolated by flash column chromatography (500 mL DCM/20 mL NH3/MeOH) to yield 10 mg of isoquinoline-3-carboxylic acid [6-cyano-4-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amide. LCMS: 424.0 (M+1)+.

Workup

filtrationthe resultant solid precipitate was filtered
washwashed with saturated NaHCO3
dissolutionThe solid was dissolved with MeOH
customevaporated onto silica gel
customisolated by flash column chromatography (500 mL DCM/20 mL NH3/MeOH)

Sources & evidence

ORD record: ord-31a84131b57f4970b137028598013c35
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893267B2

Reaction notes

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