Sodium Carbonate → HCID 66608111, compound

HRID 1910887Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]([C:11]2[N:12]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:13](=[O:22])[C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][C:15]=3Cl)[CH3:10])[N:3]=1.[CH3:29][N:30]1[CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:32]=[N:31]1.C([O-])([O-])=O.[Na+].[Na+]>CN(C)C(=O)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]([C:11]2[N:12]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:13](=[O:22])[C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][C:15]=3[C:33]2[CH:32]=[N:31][N:30]([CH3:29])[CH:34]=2)[CH3:10])[N:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

(S)-3-(1-(4-Amino-1,3,5-triazin-2-ylamino)ethyl)-8-chloro-2-phenylisoquinolin-1(2H)— one (32) (100 mg, 0.26 mmol, 1.0 eq), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (106 mg, 0.51 mmol, 2 eq), PdCl2(dppf) (16 mg, 0.02 mmol, 0.08 eq), and Na2CO3 (81 mg, 0.765 mmol, 3.0 eq) were suspended in a mixture of N,N-dimethylacetamide (20 mL) and water (1 mL). The resulting mixture was degassed and back-filled with argon three times and stirred at 120° C. under an argon atmosphere for 16 h. The mixture was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (1-4% MeOH-DCM) to afford the product, 3-((S)-1-(4-amino-1,3,5-triazin-2-ylamino)ethyl)-8-(1-methyl-1H-pyrazol-4-yl)-2-phenylisoquinolin-1(2H)-one (33). ESI-MS m/z: 439.25 [M+H]+.

Workup

customThe resulting mixture was degassed
additionback-filled with argon three times
concentrationThe mixture was concentrated in vacuo
customthe residue was purified by flash column chromatography on silica gel (1-4% MeOH-DCM)

Sources & evidence

ORD record: ord-d3f93883aa76487f98ddd481cfbabed5
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604032B2

Reaction notes

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