Tetrahydro-2,5-dimethoxyfuran-3-carbaldehyde → tert-Butyl 3-((2-(5-cyanopyrazin-2-ylamino)-5-(3-formyl-1H-pyrrol-1-yl)pyridin-4-ylamino)methyl)piperidine-1-carboxylate

HRID 556820Notes

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.C[O:33][CH:34]1[CH:38]([CH:39]=O)[CH2:37][CH:36](OC)O1>CN(C=O)C.C1(C)C=CC=CC=1>[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]([CH:34]=[O:33])=[CH:39]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 (60 mg, 0.141 mmol) (Synthesis 101-C) was dissolved in DCE/AcOH (1/1, 5 mL). 2,5-Dimethoxytetrahydrofuran-3-carboxaldehyde (28 uL, 0.211 mmol) was added and the solution was stirred at 80° C. for 1 h. The solution was evaporated to dryness and the product (143 mg, approximately 50% purity) was used without further purification.

Workup

customThe solution was evaporated to dryness
customthe product (143 mg, approximately 50% purity) was used without further purification

Sources & evidence

ORD record: ord-4fd7608047874a25aea27a575e78ae29
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058045B2

Reaction notes

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