1,1'-Carbonyldiimidazole → HCID 66635324, compound

HRID 510112Notes

Reaction equation

[NH2:1][C:2]1[C:7]([N:8]([C:10]([O:12][CH3:13])=[O:11])[NH2:9])=[C:6]([NH2:14])[N:5]=[C:4]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])[N:16]=2)[N:3]=1.C(N(CC)C(C)C)(C)C.[C:41](N1C=CN=C1)(N1C=CN=C1)=[O:42]>CN(C)C=O>[NH2:1][C:2]1[C:7]2[N:8]([C:10]([O:12][CH3:13])=[O:11])[NH:9][C:41](=[O:42])[NH:14][C:6]=2[N:5]=[C:4]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])[N:16]=2)[N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

56 mg (0.132 mmol) of the compound obtained in example 56A were initially charged in 3 ml of dimethylformamide, and 27.6 μl (0.159 mmol) of N,N-diisopropylethylamine and 25.7 mg (0.159 mmol) of carbonyldiimidazole were added. After 5 h at RT, another 27.6 μl (0.159 mmol) of N,N-diisopropylethylamine and 25.7 mg (0.159 mmol) of carbonyldiimidazole were added and the mixture was heated to 60° C. The next day, another 27.6 μl (0.159 mmol) of N,N-diisopropylethylamine and 25.7 mg (0.159 mmol) of carbonyldiimidazole were added and the mixture was heated to 60° C. for 2 further days. The reaction mixture was purified by means of preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient). 25 mg of the title compound were obtained (42% of theory).

Workup

temperaturethe mixture was heated to 60° C. for 2 further days
customThe reaction mixture was purified by means of preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient)

Sources & evidence

ORD record: ord-925c6005509446b58cb77e9e806a8419
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096592B2

Reaction notes

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