Diisopropylethylamine → HCID 69462615, compound

HRID 2416083Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[N:8]=[CH:7][C:6]([C:15]#[N:16])=[C:5]2[NH:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:20]([Cl:32])[CH:19]=1.C(N(C(C)C)CC)(C)C.[Cl:42][CH2:43][CH2:44][CH2:45][CH:46]=[CH:47][C:48](Cl)=[O:49]>O1CCCC1>[CH2:25]([O:24][C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:5]2[C:4]3[C:9](=[CH:10][C:11]([O:12][CH2:13][CH3:14])=[C:2]([NH:1][C:48](=[O:49])[CH:47]=[CH:46][CH2:45][CH2:44][CH2:43][Cl:42])[CH:3]=3)[N:8]=[CH:7][C:6]=2[C:15]#[N:16])=[CH:19][C:20]=1[Cl:32])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a stirred solution of 6-amino-4-[4-(benzyloxy)-3-chloroanilino]-7-ethoxy-3-quinolinecarbonitrile (0.89 g, 2.0 mmol) and diisopropylethylamine (0.47 ml, 2.7 mmol) in 16 ml of tetrahydrofuran at 0° C. was added a freshly-prepared solution of 6-chloro-2-hexenoyl chloride in 4 ml of tetrahydrofuran during 30 s. The mixture was then stirred at 25° C. for 2.5 h and partitioned between ethyl acetate and water. The organic layer was washed with water, dried and concentrated. The residue was chromatographed on silica gel with methylene chloride-ethyl acetate to give 0.83 g of amber solid; mass spectrum (electrospray, m/e) 574.8 (M+H)+.

Workup

custompartitioned between ethyl acetate and water
washThe organic layer was washed with water
customdried
concentrationconcentrated
customThe residue was chromatographed on silica gel with methylene chloride-ethyl acetate

Sources & evidence

ORD record: ord-bdbae0743e44419b83dda41a9f5f02f8
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06821988B2

Reaction notes

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