Potassium Carbonate → HCID 68103793, compound

HRID 869031Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[NH2:13][C:14]1[C:15]([C:32]#[C:33][C:34]2[CH:35]=[C:36]([OH:40])[CH:37]=[CH:38][CH:39]=2)=[N:16][C:17]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH:29]([CH3:31])[CH3:30])(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[CH:18][N:19]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:13][C:14]1[C:15]([C:32]#[C:33][C:34]2[CH:35]=[C:36]([CH:37]=[CH:38][CH:39]=2)[O:40][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[N:16][C:17]([C:20]2[CH:21]=[CH:22][C:23]([S:26]([CH:29]([CH3:31])[CH3:30])(=[O:28])=[O:27])=[CH:24][CH:25]=2)=[CH:18][N:19]=1

Participants

Conditions

Temperature: 65 °C

Procedure

tert-Butyl N-(3-bromopropyl)carbamate (40.86 mg, 0.1716 mmol) was added to a stirred solution of 3-[2-[3-amino-6-(4-isopropylsulfonylphenyl)pyrazin-2-yl]ethynyl]phenol (45 mg, 0.1144 mmol) and K2CO3 (39.53 mg, 0.2860 mmol) in DMF (1 mL) and the reaction mixture warmed to 65° C. for 16 hours. The reaction mixture was partitioned between DCM and saturated aqueous NaHCO3 and stirred for 5 minutes. The layers were separated by filtration through a phase separation cartridge and the aqueous layer retained was washed with DCM (×2). The combined organics were concentrated in vacuo and used directly in the next step.

Workup

customThe reaction mixture was partitioned between DCM and saturated aqueous NaHCO3
customThe layers were separated by filtration through a phase separation cartridge
washthe aqueous layer retained was washed with DCM (×2)
concentrationThe combined organics were concentrated in vacuo

Sources & evidence

ORD record: ord-1c6d98b6ea2e4a5ca319693da9231807
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969356B2

Reaction notes

Loading…