Ethylene carbonate → HCID 10152514, compound

HRID 1072084Notes

Reaction equation

HRID 1072084 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[CH:11][N:12]3[C:17]=2[C:16]([NH:18][C:19]2[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=2)[N:24]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=2)[N:23]=[CH:22]4)=[N:15][CH:14]=[N:13]3)[CH2:4][CH2:3]1.[O:36]1[CH2:40][CH2:39]OC1=O>C(Cl)Cl>[F:35][C:31]1[CH:30]=[C:29]([CH:34]=[CH:33][CH:32]=1)[CH2:28][N:24]1[C:25]2[C:21](=[CH:20][C:19]([NH:18][C:16]3[C:17]4=[C:9]([CH2:8][N:5]5[CH2:4][CH2:3][CH:2]([NH:1][CH2:39][CH2:40][OH:36])[CH2:7][CH2:6]5)[CH:10]=[CH:11][N:12]4[N:13]=[CH:14][N:15]=3)=[CH:27][CH:26]=2)[CH:22]=[N:23]1

Participants

4

Reactant 2

HCID 7303Ethylene carbonateHCID 10151881HCID 10151881, compound

Product 1

HCID 10152514HCID 10152514, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of [5-(4-amino-piperidin-1-ylmethyl)-pyrrolo[2,1-f][1,2,4]triazin-4-yl]-[1-(3-fluoro-benzyl)-1H-indazol-5-yl]-amine (188 mg, 0.4 mmole) and [1,3]dioxolan-2-one (352 mg, 10 equiv) in a sealed tube was heated at 100° C. for 3.5 h. The title compound was isolated by radial chromatography (2 mm silica gel plate, gradient elution with DCM containing 0 to 3% MeOH) afforded the title compound as a solid (43 mg, 21%); MS: 515 (M+H+); HPLC Ret Time: 1.29 min (YMC Xterra ODS S7 3.0×50 mm column, 2 min gradient, 5 ml/min).

Sources & evidence

ORD record
ord-dd2940ec2a54438ea2781c21eac146f6
Source dataset
uspto-grants-2005_06
Patent number
US06908916B2

Reaction notes

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