Acryloyl chloride → (2-{4,4-Dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}-4-[1-methyl-6-oxo-5-({6-[2-(prop-2-enamido)ethoxy]pyridin-2-yl}amino)-1,6-dihydropyridin-3-yl]pyridin-3-yl)methyl acetate

HRID 1774623Notes

Reaction equation

HRID 1774623 reaction equation
[C:1]([O:4][CH2:5][C:6]1[C:7]([N:31]2[CH2:42][CH2:41][N:40]3[C:33](=[CH:34][C:35]4[CH2:36][C:37]([CH3:44])([CH3:43])[CH2:38][C:39]=43)[C:32]2=[O:45])=[N:8][CH:9]=[CH:10][C:11]=1[C:12]1[CH:17]=[C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][CH2:27][NH2:28])[N:20]=2)[C:15](=[O:29])[N:14]([CH3:30])[CH:13]=1)(=[O:3])[CH3:2].[C:46](Cl)(=[O:49])[CH:47]=[CH2:48]>C(Cl)Cl>[C:1]([O:4][CH2:5][C:6]1[C:7]([N:31]2[CH2:42][CH2:41][N:40]3[C:33](=[CH:34][C:35]4[CH2:36][C:37]([CH3:44])([CH3:43])[CH2:38][C:39]=43)[C:32]2=[O:45])=[N:8][CH:9]=[CH:10][C:11]=1[C:12]1[CH:17]=[C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][CH2:27][NH:28][C:46](=[O:49])[CH:47]=[CH2:48])[N:20]=2)[C:15](=[O:29])[N:14]([CH3:30])[CH:13]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 13140Acryloyl chlorideHCID 118116992[4-(5-{[6-(2-Aminoethoxy)pyridin-2-yl]amino}-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridin-3-yl]methyl acetate

Product 1

HCID 118116637(2-{4,4-Dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}-4-[1-methyl-6-oxo-5-({6-[2-(prop-2-enamido)ethoxy]pyridin-2-yl}amino)-1,6-dihydropyridin-3-yl]pyridin-3-yl)methyl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 101e (250 mg, 0.387 mmol) and TEA (78 mg, 0.77 mmol) in DCM (10 mL) was added dropwise a solution of acryloyl chloride (42 mg, 0.46 mmol) in DCM. This mixture was stirred at room temperature for 2 h. The mixture was concentrated under reduce pressure to afford 101f as a yellow solid (crude), which was used in next step without further purification. MS-ESI: [M+H]+ 666.4

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-bbc8453bf7e141adbab65823f3a2ff5f
Source dataset
uspto-grants-2016_02
Patent number
US09260415B2

Reaction notes

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