HCID 58169125, compound → HCID 178437107, compound

HRID 1484901Notes

Reaction equation

HRID 1484901 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8](B2OC(C)(C)C(C)(C)O2)=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].Br[C:21]1[N:26]=[C:25]([NH:27][C:28]2[CH:32]=[C:31]([CH:33]3[CH2:35][CH2:34]3)[NH:30][N:29]=2)[C:24]([C:36]#[C:37][Si](C)(C)C)=[CH:23][N:22]=1.C1(C2NN=C(NC3C(C#C)=CN=C(C4C=C(S(N)(=O)=O)C=CC=4)N=3)C=2)CC1>[Pd]>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:21]2[N:26]=[C:25]([NH:27][C:28]3[NH:29][N:30]=[C:31]([CH:33]4[CH2:35][CH2:34]4)[CH:32]=3)[C:24]([C:36]#[CH:37])=[CH:23][N:22]=2)=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5]

Participants

5

Reactant 3

HCID 58169125HCID 58169125, compoundHCID 58169411HCID 58169411, compoundHCID 581695383-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynylpyrimidin-2-yl)benzene sulfonamide

Product 1

HCID 178437107HCID 178437107, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

2-chloro-5-(4-(3-cyclopropyl-1H-pyrazol-5-ylamino)-5-ethynylpyrimidin-2-yl) benzamide (Compound 128) (40 mg, 13%) was prepared from 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide and 2-bromo-N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-((trimethylsilyl)ethynyl) pyrimidin-4-amine using the same Pd cataliysed condition as described in Compound 110. LC-MS (m/z)=378.9 [M+H1H NMR (400 MHz, DMSO-d6): δ 0.75-0.76 (m, 2H), 0.98-0.99 (m, 2H), 1.89-1.97 (m, 1H), 4.87 (s, 1H), 6.41 (s, 1H), 7.65 (d, J=8.4 Hz, 1H), 7.72 (s, 1H), 8.05 (s, 1H), 8.31 (d, J=8.4 Hz, 1H), 8.33 (d, J=1.6 Hz, 1H), 8.58 (s, 1H), 8.75 (s, 1H), 12.33 (s, 1H).

Sources & evidence

ORD record
ord-f60be5a81e74466ba7bd8d73ee509127
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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