Ethylenediamine → HCID 71279811, compound

HRID 246564Notes

Reaction equation

[C:1]([NH:5][C:6]([C:8]1[C:12]2=[N:13][C:14]([C:17]3[C:25]4[C:20](=[CH:21][C:22]([CH2:26][CH3:27])=[CH:23][CH:24]=4)[N:19]([CH3:28])[N:18]=3)=[CH:15][N:16]=[C:11]2[N:10](COCC[Si](C)(C)C)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N)CN.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CN(C=O)C>[C:1]([NH:5][C:6]([C:8]1[C:12]2[C:11](=[N:16][CH:15]=[C:14]([C:17]3[C:25]4[C:20](=[CH:21][C:22]([CH2:26][CH3:27])=[CH:23][CH:24]=4)[N:19]([CH3:28])[N:18]=3)[N:13]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

N-tert-Butyl-2-(6-ethyl-1-methyl-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (0.03 g, 0.059 mmol), ethylenediamine (1 mL, 15.0 mmol) and TBAF (1 mL, 3.45 mmol) were combined with DMF (3.0 mL) and the reaction mixture warmed to 60° C. After 3 h, the mixture was concentrated to dryness and partitioned between ethyl acetate and water. The organic phase was concentrated in vacuo then purified by chromatography to give 2-(6-ethyl-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (5 mg, 22%). MS: (M+H)+=377; 1H NMR (DMSO-d6) δ: 12.79 (br. s., 1H), 8.96-9.28 (m, 1H), 8.19-8.49 (m, 2H), 7.97 (s, 1H), 7.57 (s, 1H), 6.98-7.25 (m, 1H), 4.16 (s, 3H), 2.81 (q, J=7.4 Hz, 2H), 1.41-1.66 (m, 9H), 1.21-1.35 (m, 3H).

Workup

concentrationthe mixture was concentrated to dryness
custompartitioned between ethyl acetate and water
concentrationThe organic phase was concentrated in vacuo
customthen purified by chromatography

Sources & evidence

ORD record: ord-1af4a34f51f8435999279df09d8f37f4
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658646B2

Reaction notes

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