Cyanoacetic acid → HCID 118389988, compound

HRID 1477968Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:13]=[C:12]([NH:14][CH:15]3[CH2:24][CH2:23][C:18]4([CH2:22][NH:21][CH2:20][CH2:19]4)[CH2:17][CH2:16]3)[CH:11]=[CH:10][N:9]=2)[CH:4]=[N:3]1.[C:25]([CH2:27][C:28](O)=[O:29])#[N:26].CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1>C(Cl)Cl.CN(C=O)C>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:13]=[C:12]([NH:14][CH:15]3[CH2:24][CH2:23][C:18]4([CH2:22][N:21]([C:28](=[O:29])[CH2:27][C:25]#[N:26])[CH2:20][CH2:19]4)[CH2:17][CH2:16]3)[CH:11]=[CH:10][N:9]=2)[CH:4]=[N:3]1

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of N2-(1-methyl-1H-pyrazol-4-yl)-N4-(2-azaspiro[4.5]decan-8-yl)pyrimidine-2,4-diamine (80 mg, 0.24 mmol) and 2-cyanoacetic acid (22 mg, 0.26 mmol) in DCM (3 mL) and DMF (2 mL) were added EDCI (49 mg, 0.26 mmol) and HOAT (17 mg, 0.12 mmol). The mixture was stirred at 45° C. for 1 h then concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=10/1) to give the product as a yellow solid (13 mg, 13%).

Workup

concentrationthen concentrated in vacuo
customThe residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=10/1)

Sources & evidence

ORD record: ord-0b0997bdc48a48f8b8850f43cbfda9ce
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403801B2

Reaction notes

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