1-Cyclopropyl-3-(2-fluoro-4-iodo-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid (2-vinyloxy-ethoxy)-amide → 1-Cyclopropyl-3-(2-fluoro-4-methylsulfanyl-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid (2-vinyloxy-ethoxy)-amide
Reaction equation
[CH:1]([O:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[N:18]([CH:19]2[CH2:21][CH2:20]2)[C:17]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[C:11]=1[NH:22][C:23]1[CH:28]=[CH:27][C:26](I)=[CH:25][C:24]=1[F:30])=[O:9])=[CH2:2].COC(C1N(C2CC2)C2C=CN=CC=2C=1NC1C=C[C:51]([S:54]C)=CC=1F)=O>>[CH:1]([O:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[N:18]([CH:19]2[CH2:21][CH2:20]2)[C:17]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[C:11]=1[NH:22][C:23]1[CH:28]=[CH:27][C:26]([S:54][CH3:51])=[CH:25][C:24]=1[F:30])=[O:9])=[CH2:2]Participants
Reactant 2
Product 1
Procedure
This compound was prepared in an analogous fashion to 1-cyclopropyl-3-(2-fluoro-4-iodo-phenylamino)-1H-pyrrolo[3,2-c]-pyridine-2-carboxylic acid (2-vinyloxy-ethoxy)-amide, using 1-cyclopropyl-3-(2-fluoro-4-methylsulfanyl-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid methyl ester as the starting material. 1H-NMR (500 MHz, CDCl3) δ ppm 9.50 (br s, 1H), 8.60 (d, J=0.88 Hz, 1H), 8.38 (d, J=5.97 Hz, 1H), 7.46 (dd, J=5.98 Hz, 1H), 7.10 (dd, J=11.45 Hz, 1H), 6.89 (dd, J=8.41 Hz, 1H), 6.66 (t, J=8.67 Hz, 1H), 6.42 (dd, J=14.33 Hz, 1H), 6.33 (br s, 1H), 4.29-4.22 (m, 2H), 4.18 (dd, J=14.33 Hz, 1H), 4.04 (dd, J=6.82 Hz, 1H), 3.98-3.90 (m, 2H), 3.61-3.53 (m, 1H), 2.44 (s, 3H), 1.33-1.20 (m, 2H), 1.01-0.96 (m, 2H); LC-MS (method D): [M+H]+=443.3, RT=2.17 min.
Sources & evidence
- ORD record
- ord-6afaea5489b1477f9f04924ec69be55a
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07855216B2
Reaction notes
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