Triethylamine → HCID 66614413, compound

HRID 510125Notes

Reaction equation

[CH:1]1([NH:5][C:6]2[C:7]([NH2:30])=[N:8][C:9]([C:13]3[C:21]4[C:16](=[N:17][CH:18]=[CH:19][CH:20]=4)[N:15]([CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[F:29])[N:14]=3)=[N:10][C:11]=2[NH2:12])[CH2:4][CH2:3][CH2:2]1.C1N=CN([C:36](N2C=NC=C2)=[O:37])C=1.C(N(CC)CC)C>CN(C)C=O>[NH2:12][C:11]1[N:10]=[C:9]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[N:15]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[F:29])[N:14]=2)[N:8]=[C:7]2[C:6]=1[N:5]([CH:1]1[CH2:4][CH2:3][CH2:2]1)[C:36](=[O:37])[NH:30]2

Participants

Conditions

Temperature: 100 °C

Procedure

133 mg (0.26 mmol) of the compound from example 65A were initially charged in dimethylformamide (1.4 ml), then 213 mg (1.32 mmol) of N,N-carbonyldiimidazole and 0.44 ml (3.16 mmol) of triethylamine were added and the mixture was stirred at 100° C. overnight. Thereafter, another 200 mg (1.23 mmol) of N,N-carbonyldiimidazole were added and the mixture was again stirred at 100° C. overnight. The reaction mixture was purified directly by means of preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid gradient). This gave 79 mg (68% of theory) of the title compound in solid form.

Workup

stirringthe mixture was again stirred at 100° C. overnight
customThe reaction mixture was purified directly by means of preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid gradient)

Sources & evidence

ORD record: ord-d8efb322f3454db2b572492f8b30246f
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096592B2

Reaction notes

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