HCID 58169125, compound → HCID 50943528, compound

HRID 1484902Notes

Reaction equation

HRID 1484902 reaction equation
C1(C2NN=C(NC3C(C#C)=CN=C(C4C=C(S(N)(=O)=O)C=CC=4)N=3)C=2)CC1.Br[C:29]1[N:34]=[C:33]([NH:35][C:36]2[CH:40]=[C:39]([CH:41]3[CH2:43][CH2:42]3)[NH:38][N:37]=2)[C:32]([C:44]#[C:45][Si](C)(C)C)=[CH:31][N:30]=1.[CH3:50][C:51]1[CH:59]=[CH:58][C:57](B2OC(C)(C)C(C)(C)O2)=[CH:56][C:52]=1[C:53]([NH2:55])=[O:54]>>[CH:41]1([C:39]2[NH:38][N:37]=[C:36]([NH:35][C:33]3[C:32]([C:44]#[CH:45])=[CH:31][N:30]=[C:29]([C:57]4[CH:58]=[CH:59][C:51]([CH3:50])=[C:52]([CH:56]=4)[C:53]([NH2:55])=[O:54])[N:34]=3)[CH:40]=2)[CH2:43][CH2:42]1

Participants

4

Reactant 3

HCID 58169125HCID 58169125, compoundHCID 581694502-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 581695383-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynylpyrimidin-2-yl)benzene sulfonamide3×

Product 1

HCID 50943528HCID 50943528, compound

Procedure

Using the same coupling procedure as described in Compound 110, 5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynylpyrimidin-2-yl)-2-methyl benzamide (Compound 110) (7.4 mg, 2.6%) was prepared from 2-bromo-N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-((trimethylsilyl)ethynyl) pyrimidin-4-amine and 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide. LC-MS (m/z)=359.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.74-0.78 (m, 2H), 0.95-1.00 (m, 2H), 1.91-1.95 (m, 1H), 2.43 (s, 3H), 4.88 (s, 1H), 6.47 (s, 1H), 7.39 (d, J=8.0 Hz, 1H), 7.49 (s, 1H), 7.91 (s, 1H), 8.24 (d, J=8.0 Hz, 1H), 8.33 (d, J=1.2 Hz, 1H), 8.57 (s, 1H), 8.73 (s, 1H), 12.37 (bs, 1H).

Sources & evidence

ORD record
ord-f01c89bd4914449b8d35041f271e0083
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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