5-[(3-amino-1-methyl-1H-indazol-6-yl)oxy]-3-(4-methoxybenzyl)-3,4-dihydropyrido[2,3-d]pyrimidin-2(1H)-one → 5-(3-Amino-1-methyl-1H-indazol-6-yloxy)-3,4-dihydro-1H-pyrido[2,3-d]pyrimidin-2-one

HRID 1045505

Reaction equation

[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12]3[C:21]4[CH2:20][N:19](CC5C=CC(OC)=CC=5)[C:18](=[O:31])[NH:17][C:16]=4[N:15]=[CH:14][CH:13]=3)=[CH:8][CH:9]=2)[N:4]([CH3:32])[N:3]=1>FC(F)(F)C(O)=O>[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12]3[C:21]4[CH2:20][NH:19][C:18](=[O:31])[NH:17][C:16]=4[N:15]=[CH:14][CH:13]=3)=[CH:8][CH:9]=2)[N:4]([CH3:32])[N:3]=1

Participants

Conditions

Temperature: 75 °C

Procedure

Compound 276 (25.00 mg; 0.06 mmol; 1.00 eq.) was dissolved in trifluoroacetic acid (2.00 ml). The vessel was sealed and heated at 75 degrees C. for two days. The reaction was concentrated, redissolved in DMSO, treated with Et3N to get pH ˜8, and then purified via prep HPLC to afford 17mg (69%) of 277 as a white solid. LC-MS (M+H=311, obsd.=311).

Workup

customThe vessel was sealed
concentrationThe reaction was concentrated
dissolutionredissolved in DMSO
additiontreated with Et3N
customto get pH ˜8
custompurified via prep HPLC

Sources & evidence

ORD record: ord-5a7ae7da25594a88a6ea16db24a514cd
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569295B2

Linked notes

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