2,6-Lutidine → HCID 86658561, compound

HRID 1520207Notes

Reaction equation

HRID 1520207 reaction equation
[B-](F)(F)(F)F.[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+]([F:21])(CC2)C1.[CH3:22][O:23][C:24]1[CH:48]=[CH:47][C:27]([CH2:28][N:29]2[CH:33]=[C:32]([C:34]3[N:35]=[C:36]([NH:39][C:40]4[CH:45]=[CH:44][C:43]([F:46])=[CH:42][N:41]=4)[S:37][CH:38]=3)[CH:31]=[N:30]2)=[CH:26][CH:25]=1.CC1C=CC=C(C)N=1>CN(C=O)C>[CH3:22][O:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:28][N:29]2[CH:33]=[C:32]([C:34]3[N:35]=[C:36]([NH:39][C:40]4[CH:45]=[CH:44][C:43]([F:46])=[CH:42][N:41]=4)[S:37][C:38]=3[F:21])[CH:31]=[N:30]2)=[CH:47][CH:48]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 2724933SelectfluorHCID 87398437HCID 87398437, compound

Product 1

HCID 86658561HCID 86658561, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to Scheme 7 Step 1: Selectfluor (3.28 mmol, 1.16 g) was added portionwise to a solution of N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)thiazol-2-yl)-5-fluoropyridin-2-amine (2.18 mmol, 833 mg) and of 2,6-dimethylpyridine (2.18 mmol, 0.25 mL) in DMF (25 mL) at 0° C. The reaction mixture was stirred at room temperature for 12 hours. The reaction was quenched with water (70 mL). A precipitate was formed, was filtered and was dried to yield N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-fluorothiazol-2-yl)-5-fluoropyridin-2-amine (1.85 mmol, 739 mg, 85%).

Workup

  1. customThe reaction was quenched with water (70 mL)
  2. customA precipitate was formed
  3. filtrationwas filtered
  4. customwas dried

Sources & evidence

ORD record
ord-d65571ebd5a2498ea9677719dab05e15
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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