N-Boc-N-methylethylenediamine → HCID 59212702, compound

HRID 222989Notes

Reaction equation

HRID 222989 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16](S(C)=O)[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:32]=[CH:33][C:34]=3[CH3:35])[C:22]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[O:23])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:39].[NH2:40][CH2:41][CH2:42][N:43]([CH3:51])[C:44](=[O:50])[O:45][C:46]([CH3:49])([CH3:48])[CH3:47]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([NH:40][CH2:41][CH2:42][N:43]([CH3:51])[C:44](=[O:50])[O:45][C:46]([CH3:47])([CH3:48])[CH3:49])[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([C:22]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)=[O:23])[CH:32]=[CH:33][C:34]=3[CH3:35])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:39]

Participants

4

Reactant 2

HCID 2756424N-Boc-N-methylethylenediamineHCID 59212706HCID 59212706, compound

Product 1

HCID 59212702HCID 59212702, compoundYield 102.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[8-(2,6-difluorophenyl)-2-(methylsulfinyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-N-(4-fluorophenyl)-4-methylbenzamide (50 mg, 0.09 mmol) in DCM (5 mL) was added 1,1-dimethylethyl (2-aminoethyl)-methylcarbamate (0.09 mL, 0.5 mmol). The resultant mixture was stirred at room temperature overnight. The mixture was concentrated under vacuo. Flash chromatography (90% CH2Cl2/7% MeOH/3% NH4OH) then provide the title compound (61 mg, 100%). LC-MS (ES) m/z 659 (M+H)+; 1H-NMR(CDCl3) δ 1.39 (s, 9H), 1.70 (br, 1H), 2.32 (s, 3H), 2.65 (s, 2H), 2.82 (s, 2H), 3.22 (s, 3H), 3.60 (br, 1H), 6.34 (d, 1H), 7.03 (m, 4H), 7.34 (m, 1H), 7.48 (m, 2H), 7.64 (m, 1H), 7.84 (m, 2H), 8.14 (d, 1H).

Workup

  1. concentrationThe mixture was concentrated under vacuo

Sources & evidence

ORD record
ord-da6adb5993ea4ff889de99d2a53e2452
Source dataset
uspto-grants-2012_06
Patent number
US08207176B2

Reaction notes

Loading…