4-Methoxybenzenesulfonyl chloride → (S)-N-(5-(4-Amino-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidin-5-yl)pyridin-3-yl)-4-methoxybenzenesulfonamide

HRID 1052470Notes

Reaction equation

HRID 1052470 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]([C:11]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:23])[C:14]3=[C:24]([CH3:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[C:3]=1Br.[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([S:37]([NH:40][C:41]2[CH:42]=[N:43][CH:44]=[C:45](B3OC(C)(C)C(C)(C)O3)[CH:46]=2)(=[O:39])=[O:38])=[CH:33][CH:32]=1.CC1(C)C(C)(C)OB(C2C=C(N)C=NC=2)O1.COC1C=CC(S(Cl)(=O)=O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(P([Pd-4](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:1][C:2]1[C:3]([C:45]2[CH:46]=[C:41]([NH:40][S:37]([C:34]3[CH:35]=[CH:36][C:31]([O:30][CH3:29])=[CH:32][CH:33]=3)(=[O:39])=[O:38])[CH:42]=[N:43][CH:44]=2)=[C:4]([NH:8][C@H:9]([C:11]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:23])[C:14]3=[C:24]([CH3:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[N:5]=[CH:6][N:7]=1

Participants

7

Reactant 5

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 438110685-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamineHCID 66524682HCID 66524682, compoundHCID 118433733HCID 118433733, compound

Product 1

HCID 118433907(S)-N-(5-(4-Amino-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidin-5-yl)pyridin-3-yl)-4-methoxybenzenesulfonamideYield 76%

Reagents, catalysts & solvents 1

HCID 178420553HCID 178420553, compoundCatalyst

Procedure

(S)-2-(1-((6-Amino-5-bromopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (65 mg, 0.15 mmol) was treated with 4-methoxy-N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide (87 mg, 0.22 mmol, prepared from 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine, as described in WO 2009155527 A2 20091223, and 4-methoxybenzene-1-sulfonyl chloride according to the method described In Preparation 15b), 2M sodium carbonate (221 μl, 0.44 mmol) and tetrakis(triphenylphosphino)palladium(0) (9 mg, 0.01 mmol) according to the method described in Example 3 to give 92 mg (76% yield) of the title compound as a solid. Purity 53%.

Sources & evidence

ORD record
ord-411a58edecbe435290b6be2f51f96a37
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

Loading…