Ethylenediamine → HCID 57537536, compound

HRID 1693724Notes

Reaction equation

[NH2:1][C:2]1[N:12]=[CH:11][C:10]([C:13]2[C:14]([Cl:40])=[C:15]3[C:21]([C:22]4[CH:27]=[C:26]([F:28])[C:25]([F:29])=[CH:24][C:23]=4[O:30][CH3:31])=[CH:20][N:19](COCC[Si](C)(C)C)[C:16]3=[N:17][CH:18]=2)=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5].C(N)CN>FC(F)(F)C(O)=O>[NH2:1][C:2]1[N:12]=[CH:11][C:10]([C:13]2[C:14]([Cl:40])=[C:15]3[C:21]([C:22]4[CH:27]=[C:26]([F:28])[C:25]([F:29])=[CH:24][C:23]=4[O:30][CH3:31])=[CH:20][NH:19][C:16]3=[N:17][CH:18]=2)=[CH:9][C:3]=1[C:4]([N:6]([CH3:7])[CH3:8])=[O:5]

Participants

Conditions

Temperature: 23 °C

Procedure

2-Amino-5-[4-chloro-3-(4,5-difluoro-2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-nicotinamide (76 mg, 0.136 mmol) was dissolved in trifluoroacetic acid (3 mL) and stirred at 23° C. for 45 minutes. The solution was concentrated under vacuum and taken up in methanol (10 mL). Ethylenediamine (100 μL, 5.39 mmol) was added, and the mixture was stirred at 35° C. for 20 minutes. Methanol was removed under vacuum. The crude was taken up in methanol (0.5 mL) and water (1 mL) was added. The resulting precipitate was collect by filtration to afford 2-Amino-5-[4-chloro-3-(4,5-difluoro-2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-nicotinamide (49.6 mg, 0.108 mmol, 80% yield). 1H-NMR [500 MHz, d6-DMSO] δ: 8.18 (s, 1H), 8.05 (d, 1H), 7.56 (s, 1H), 7.47 (d, 1H), 7.35 (m, 1H), 7.15 (m, 1H), 6.15 (s, 2H), 6.68 (s, 2H), 2.95 (s, 6H); MS [MH+] m/z: 458.

Workup

concentrationThe solution was concentrated under vacuum
stirringthe mixture was stirred at 35° C. for 20 minutes
customMethanol was removed under vacuum
additionwater (1 mL) was added
filtrationThe resulting precipitate was collect by filtration

Sources & evidence

ORD record: ord-95893d7a6abe46b2aa03721186e14a19
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158647B2

Reaction notes

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