Hydrochloric Acid → 3-cyclobutyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)imidazo[1,5-a]pyrazin-8-amine

HRID 2076569Notes

Reaction equation

HRID 2076569 reaction equation
[CH:1]1([C:5]2[N:9]3[CH:10]=[CH:11][N:12]=[C:13]([NH2:14])[C:8]3=[C:7]([C:15]3[N:23](COCC[Si](C)(C)C)[C:18]4=[N:19][CH:20]=[CH:21][CH:22]=[C:17]4[CH:16]=3)[N:6]=2)[CH2:4][CH2:3][CH2:2]1.Cl>>[CH:1]1([C:5]2[N:9]3[CH:10]=[CH:11][N:12]=[C:13]([NH2:14])[C:8]3=[C:7]([C:15]3[NH:23][C:18]4=[N:19][CH:20]=[CH:21][CH:22]=[C:17]4[CH:16]=3)[N:6]=2)[CH2:2][CH2:3][CH2:4]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 591330243-Cyclobutyl-1-[1-(2-trimethylsilylethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]imidazo[1,5-a]pyrazin-8-amine

Product 1

HCID 166792573-cyclobutyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)imidazo[1,5-a]pyrazin-8-amine

Procedure

3-Cyclobutyl-1-[1-(2-trimethylsilylethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]imidazo[1,5-a]pyrazin-8-amine (35 mg, 0.08 mmol) was stirred with concentrated HCl for 15 min. The mixture was thien concentrated in vacuo and purified via mass directed preparative HPLC to afford the title compound. 1H NMR (400 MHz DMSO-d6) δ 1.92-2.00 (m, 1H), 2.07-2.14 (m, 1H), 2.43-2.47 (m, 4H), 3.93-4.01 (m, 1H), 6.35-6.49 (Us, 2H), 6.64-6.70 (m, 1H), 7.03-7.10 (m, 2H), 7.39-7.49 (m, 1H), 7.95-8.00 (m, 1H), 8.18-8.23 (m, 1H), 11.91 (bs, 1H). MS (ES+): m/z: 305.17 [MH+].

Workup

  1. concentrationThe mixture was thien concentrated in vacuo
  2. custompurified via mass

Sources & evidence

ORD record
ord-2f8356ada8204b3b8dc3950ee8804fe4
Source dataset
uspto-grants-2011_04
Patent number
US07923555B2

Reaction notes

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