Triethylamine → HCID 59747866, compound

HRID 746459Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([NH:17][C:18]3[CH:26]=[C:25]4[C:21]([CH:22]=[CH:23][NH:24]4)=[CH:20][CH:19]=3)[C:11]3[N:12]([CH:14]=[CH:15][N:16]=3)[CH:13]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:34]([C:38]1[CH:46]=[CH:45][C:41]([C:42](Cl)=[O:43])=[CH:40][CH:39]=1)([CH3:37])([CH3:36])[CH3:35]>C1COCC1>[C:34]([C:38]1[CH:39]=[CH:40][C:41]([C:42]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[N:9]=[C:10]([NH:17][C:18]4[CH:26]=[C:25]5[C:21]([CH:22]=[CH:23][NH:24]5)=[CH:20][CH:19]=4)[C:11]4[N:12]([CH:14]=[CH:15][N:16]=4)[CH:13]=3)[CH:3]=2)=[O:43])=[CH:45][CH:46]=1)([CH3:37])([CH3:35])[CH3:36]

Participants

Conditions

Temperature: 0 °C

Procedure

After dissolving 0.34 g (1 mmole) [6-(3-amino-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-(1H-indol-6-yl)-amine in 20 mL anhydrous THF, 3 equivalents of triethylamine are added and the reaction solution is cooled to 0° C. A solution of 0.2 g of 4-tert-butyl-benzoyl chloride (1 mmole) in 5 mL THF is added dropwise to the 0° C. reaction solution under N2. The ice bath is removed and the reaction is allowed to warm slowly to rt for 1 hr. Diethyl ether is then added slowly to the reaction solution and the resulting solid filtered and washed with diethyl ether to provide pure 4-tert-butyl-N-{3-[8-(1H-indol-6-ylamino)-imidazo[1,2-a]pyrazin-6-yl]-phenyl}-benzamide.

Workup

additionare added
customThe ice bath is removed
temperatureto warm slowly to rt for 1 hr
additionDiethyl ether is then added slowly to the reaction solution
filtrationthe resulting solid filtered
washwashed with diethyl ether

Sources & evidence

ORD record: ord-4b5d73928d9a4842830ceed0d2786164
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07393848B2

Reaction notes

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