Triethylamine → HCID 66635322, compound

HRID 510127Notes

Reaction equation

[F:1][C:2]1[CH:34]=[CH:33][CH:32]=[CH:31][C:3]=1[CH2:4][NH:5][C:6]1[C:7]([NH2:30])=[N:8][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:10][C:11]=1[NH2:12].C1N=CN([C:40](N2C=NC=C2)=[O:41])C=1.C(N(CC)CC)C>CN(C)C=O>[NH2:30][C:7]1[N:8]=[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:10]=[C:11]2[C:6]=1[N:5]([CH2:4][C:3]1[CH:31]=[CH:32][CH:33]=[CH:34][C:2]=1[F:1])[C:40](=[O:41])[NH:12]2

Participants

Conditions

Temperature: 100 °C

Procedure

268 mg (0.48 mmol) of the compound from example 66A were initially charged in dimethylformamide (2.6 ml), then 389 mg (2.40 mmol) of N,N-carbonyldiimidazole and 0.80 ml (5.75 mmol) of triethylamine were added and the mixture was stirred at 100° C. overnight. Subsequently, 380 mg (2.34 mmol) of N,N-carbonyldiimidazole were added and the mixture was stirred again 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 130 mg (56% of theory) of the title compound.

Workup

stirringthe mixture was stirred again 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-7ae2d8c4e1da4a82946ecf7a4f8aefe2
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096592B2

Reaction notes

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