HCID 67283272, compound → HCID 178428227, compound

HRID 1253813Notes

Reaction equation

HRID 1253813 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([SH:13])[CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.[Cl:14][C:15]1[N:20]=[C:19](S(C)(=O)=O)[N:18]=[C:17]([NH:25][C:26]2[NH:30][N:29]=[C:28]([CH3:31])[CH:27]=2)[CH:16]=1>CC(O)(C)C>[Cl:14][C:15]1[N:20]=[C:19]([S:13][C:4]2[CH:5]=[C:6]3[C:11](=[C:2]([F:1])[CH:3]=2)[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]3)[N:18]=[C:17]([NH:25][C:26]2[NH:30][N:29]=[C:28]([CH3:31])[CH:27]=2)[CH:16]=1

Participants

4

Reactant 2

HCID 67283272HCID 67283272, compoundHCID 178428229HCID 178428229, compound

Product 1

HCID 178428227HCID 178428227, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 8-fluoro-2-methylquinoline-6-thiol (1.21 g, 6.27 mmol) in tBuOH (25 ml) was added 6-chloro-N-(3-methyl-1H-pyrazol-5-yl)-2-(methylsulfonyl)pyrimidin-4-amine (1.5 g, 5.22 mmol). The reaction mixture was degassed three times (vacuum/N2) before being heated to 90° C. for 18 hours. The crude mixture was partially concentrated in vacuo. The resulting solid was filtered and washed with ethyl acetate and an aqueous solution of K2CO3. The solid was dried in a pistol under vacuo to afford the title compound as an off-white solid (1.029 g, 49% yield). 1H NMR (DMSO D6, 400 MHz) δ1.42 (3H, br s), 2.73 (3H, s), 4.95 (1H, br s), 6.47 (1H, br s), 7.61 (1H, d), 7.78 (1H, dd), 8.14 (1H, s), 8.39 (1H, d), 10.32 (1H, br s), 11.75 (1H, br s); MS (ES+) 401, (ES−) 399.

Workup

  1. customThe reaction mixture was degassed three times (vacuum/N2)
  2. concentrationThe crude mixture was partially concentrated in vacuo
  3. filtrationThe resulting solid was filtered
  4. washwashed with ethyl acetate
  5. customThe solid was dried in a pistol under vacuo

Sources & evidence

ORD record
ord-d04204572c734465a0ca2af1aa1294c4
Source dataset
uspto-grants-2013_06
Patent number
US08455507B2

Reaction notes

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