HCID 58169125, compound → HCID 178437111, compound

HRID 1484900Notes

Reaction equation

HRID 1484900 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10](B2OC(C)(C)C(C)(C)O2)[CH:9]=1)(=[O:7])=[O:6].Br[C:24]1[N:29]=[C:28]([NH:30][C:31]2[CH:35]=[C:34]([CH:36]3[CH2:38][CH2:37]3)[NH:33][N:32]=2)[C:27]([C:39]#[C:40][Si](C)(C)C)=[CH:26][N:25]=1.C1(C2NN=C(NC3C(C#C)=CN=C(C4C=C(S(N)(=O)=O)C=CC=4)N=3)C=2)CC1>[Pd]>[CH:36]1([C:34]2[CH:35]=[C:31]([NH:30][C:28]3[C:27]([C:39]#[CH:40])=[CH:26][N:25]=[C:24]([C:10]4[CH:9]=[C:8]([S:5]([NH:4][CH2:3][CH2:2][OH:1])(=[O:6])=[O:7])[CH:13]=[CH:12][CH:11]=4)[N:29]=3)[NH:32][N:33]=2)[CH2:38][CH2:37]1

Participants

5

Reactant 3

HCID 58169125HCID 58169125, compoundHCID 58169322HCID 58169322, compoundHCID 581695383-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynylpyrimidin-2-yl)benzene sulfonamide

Product 1

HCID 178437111HCID 178437111, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

3-(4-(3-Cyclopropyl-1H-pyrazol-5-ylamino)-5-ethynylpyrimidin-2-yl)-N-(2-hydroxyethyl)benzene sulfonamide (Compound 122) (100 mg, 22%) was prepared from N-(2-hydroxyethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide 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)=425.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.81-0.83 (m, 2H), 0.96-0.98 (m, 2H), 1.91-1.98 (m, 1H), 2.83 (q, J=6.0 Hz, 2H), 3.37 (q, J=6.0 Hz, 2H), 4.70 (t, J=5.6 Hz, 1H), 4.91 (s, 1H), 6.46 (s, 1H), 7.71 (t, J=5.6 Hz, 1H), 7.94 (d, J=8.0 Hz, 1H), 8.52 (d, J=7.6 Hz, 1H), 8.62 (s, 1H), 8.73 (s, 1H), 8.76 (s, 1H), 12.32 (s, 1H).

Sources & evidence

ORD record
ord-c685c9d519f14482b93d64cac6757a97
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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