Triethylamine → 1,1-Dimethylethyl (2-{[8-(2,6-difluorophenyl)-4-(2-methyl-5-{[(2-phenylethyl)amino]carbonyl}phenyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-2-yl]amino}ethyl)methylcarbamate

HRID 223088Notes

Reaction equation

HRID 223088 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:33]=[CH:34][C:35]=3[CH3:36])[C:22]([NH:24][CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:23])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:40].[NH2:41][CH2:42][CH2:43][N:44]([CH3:52])[C:45](=[O:51])[O:46][C:47]([CH3:50])([CH3:49])[CH3:48].C(N(CC)CC)C>ClCCl>[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:41][CH2:42][CH2:43][N:44]([CH3:52])[C:45](=[O:51])[O:46][C:47]([CH3:48])([CH3:49])[CH3:50])[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([C:22]([NH:24][CH2:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[O:23])[CH:33]=[CH:34][C:35]=3[CH3:36])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:40]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2756424N-Boc-N-methylethylenediamineHCID 592126813-[8-(2,6-difluorophenyl)-2-(methylsulfinyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-4-methyl-N-(2-phenylethyl)benzamide

Product 1

HCID 592126871,1-Dimethylethyl (2-{[8-(2,6-difluorophenyl)-4-(2-methyl-5-{[(2-phenylethyl)amino]carbonyl}phenyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-2-yl]amino}ethyl)methylcarbamateYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 3-[8-(2,6-difluorophenyl)-2-(methylsulfinyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-4-methyl-N-(2-phenylethyl)benzamide (156 mg, 0.28 mmol) in dichloromethane (11 mL) was added 1,1-dimethylethyl (2-aminoethyl)methylcarbamate (75 μL, 0.42 mmol) and triethylamine (78.7 μL, 0.56 mmol). The reaction mixture was stirred at room temperature for 16 hours then applied to the flash chromatograph to afford the titled compound 147 mg (79%). LC-MS m/z 669 (M+H)+; 1H-NMR (MeOD) 1.30 (m, 9H), 2.31 (m, 3H), 2.65 (m, 2H), 2.76 (m, 1H), 2.92 (m, 2H), 3.22 (m, 2H), 3.45 (m, 1H), 3.60 (m, 2H), 6.35 (m, 1H), 7.19 (m, 2H), 7.26 (m, 5H), 7.43 (m, 1H), 7.49 (m, 1H), 7.60 (m, 1H), 7.74 (m, 1H), 7.97 (m, 1H).

Sources & evidence

ORD record
ord-8f8bdc0e607a46729393c050e5ffdfd3
Source dataset
uspto-grants-2012_06
Patent number
US08207176B2

Reaction notes

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