Methylamine → HCID 19389969, compound

HRID 1757150Notes

Reaction equation

HRID 1757150 reaction equation
[NH2:1][C:2]1([CH2:14][OH:15])[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.CN.[F:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:20]=1[C:21](Cl)=[O:22]>C1COCC1>[F:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:20]=1[C:21]([NH:1][C:2]1([CH2:14][OH:15])[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1)=[O:22]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 874382,6-Difluorobenzoyl chlorideHCID 19389970HCID 19389970, compound

Product 1

HCID 19389969HCID 19389969, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring mixture of 2.0 g (0.00965 mol) of the product of Step C, 976 mg (0.00965 mol) of methylamine in 30 mL of THF at 0° C. was added dropwise a solution of 2,6-difluorobenzoylchloride in 15 mL of THF. The reaction mixture was stirred at ambient temperature for 30 minutes. The precipitated triethylamine hydrochloride was filtered off and the filtrate concentrated. It was purified by passing through a silica gel column eluting with EtOAc:Hexane (2:3) to afford a white solid: mp 174°-175° C. 1H NMR (CDCl3) d 7.30 (m, 2H), 6.90 (t, 2H), 6.85 (dd, 1H), 6.60 (d, 1H), 6.35 (broad s, 1H), 4.80 (dd, 1H), 4.20 (dd, 1H), 3.77 (s, 3H), 3.75 (d, 2H), 2.80 (m, 2H), 2.30 (m, 2H), 1.90 (m, 2H).

Workup

  1. filtrationThe precipitated triethylamine hydrochloride was filtered off
  2. concentrationthe filtrate concentrated
  3. customIt was purified
  4. washeluting with EtOAc:Hexane (2:3)
  5. customto afford a white solid

Sources & evidence

ORD record
ord-0dccc3d33627422d9afb6f0854b98a7c
Source dataset
uspto-grants-1995_08
Patent number
US05444079

Reaction notes

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