Triethylamine → HCID 22051000, compound

HRID 1832099Notes

Reaction equation

HRID 1832099 reaction equation
[Br:1][C:2]1[C:3](=[O:29])[N:4]([CH2:19][C:20]2[CH:25]=[N:24][C:23]([CH2:26][NH:27][CH3:28])=[CH:22][N:21]=2)[C:5]([CH3:18])=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17].C(N(CC)CC)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>C(#N)C>[Br:1][C:2]1[C:3](=[O:29])[N:4]([CH2:19][C:20]2[N:21]=[CH:22][C:23]([CH2:26][N:27]([CH3:28])[S:38]([CH3:37])(=[O:40])=[O:39])=[N:24][CH:25]=2)[C:5]([CH3:18])=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22050409HCID 22050409, compound

Product 1

HCID 22051000HCID 22051000, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 3-bromo-4-[(2,4-difluorobenzyl)oxy]-6-methyl-1-({5-[(methylamino)methyl]pyrazin-2-yl}methyl)pyridin-2(1H)-one (0.16 g, 0.34 mmol) in acetonitrile at 0° C. was added triethylamine (0.043 g, 0.42 mmol), followed by the addition of methane sulfonylchloride (0.047 g, 0.41 mmol) and stirred at room temperature for 1 h under argon atmosphere. The solvents were removed in vacuo and the residue was triturated with water and filtered. It was washed with water an, acetonitrile and dried in vacuo to afford 0.11 g of material. 1H NMR (CD3OD/400 MHz) δ 8.62 (s, 1H), 8.55 (s, 1H), 7.61 (m, 1H), 7.0 (m, 2H), 6.53 (s, 1H), 5.47 (s, 2H), 5.29 (s, 2H), 4.49 (s, 2H), 2.95 (s, 3H), 2.85 (s, 3H), and 2.55 (s, 3H); 19F NMR (CD3OD/400 MHz) −111.70 (m) and −116.07 (m); ES-HRMS m/z 543.0515 (M+H calcd for C21H22BrF2N4O4S requires 543.0508).

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was triturated with water
  3. filtrationfiltered
  4. washIt was washed with water an, acetonitrile
  5. customdried in vacuo

Sources & evidence

ORD record
ord-714d19e3f6fb497d8b631fe3250d9c12
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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