Ethyl 2,5-dimethoxy-tetrahydrofuran-3-carboxylate → tert-Butyl 3-((2-(5-cyanopyrazin-2-ylamino)-5-(3-(ethoxycarbonyl)-1H-pyrrol-1-yl)pyridin-4-ylamino)methyl)piperidine-1-carboxylate

HRID 384664Notes

Reaction equation

[NH2:1][C:2]1[C:3]([NH:17][CH2:18][CH:19]2[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:20]2)=[CH:4][C:5]([NH:8][C:9]2[CH:14]=[N:13][C:12]([C:15]#[N:16])=[CH:11][N:10]=2)=[N:6][CH:7]=1.CO[CH:34]1[CH:38]([C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:37][CH:36](OC)O1>C(O)(=O)C>[C:15]([C:12]1[N:13]=[CH:14][C:9]([NH:8][C:5]2[CH:4]=[C:3]([NH:17][CH2:18][CH:19]3[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:20]3)[C:2]([N:1]3[CH:36]=[CH:37][C:38]([C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:34]3)=[CH:7][N:6]=2)=[N:10][CH:11]=1)#[N:16]

Participants

Conditions

Temperature: 80 °C

Procedure

tert-Butyl 3-((5-amino-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylate (163 mg, 0.384 mmol) (Synthesis 101-C) and ethyl 2,5-dimethoxy-tetrahydrofuran-3-carboxylate (196 mg, 0.96 mmol) were dissolved in acetic acid (4 mL) and the solution was stirred at 80° C. for 6.5 h. The reaction mixture was evaporated to dryness and the residue was used directly in the next step.

Workup

customThe reaction mixture was evaporated to dryness

Sources & evidence

ORD record: ord-ee4b1c7cbd714e9f90cde4e02245ec3e
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367658B2

Reaction notes

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