Triethylamine → HCID 21035306, compound

HRID 1832129Notes

Reaction equation

HRID 1832129 reaction equation
[Br:1][C:2]1[C:3](=[O:34])[N:4]([C:19]2[CH:20]=[C:21]([NH:26][C:27](=[O:33])OC(C)(C)C)[CH:22]=[CH:23][C:24]=2[F:25])[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.[C:42]([O:45][CH2:46]C(Cl)=O)(=[O:44])[CH3:43].[Cl-].[NH4+]>O1CCCC1>[C:42]([O:45][CH2:46][C:27]([NH:26][C:21]1[CH:22]=[CH:23][C:24]([F:25])=[C:19]([N:4]2[C:5]([CH3:18])=[CH:6][C:7]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=3[F:17])=[C:2]([Br:1])[C:3]2=[O:34])[CH:20]=1)=[O:33])(=[O:44])[CH3:43]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 26297Acetoxyacetyl chlorideHCID 22050673HCID 22050673, compound

Product 1

HCID 21035306HCID 21035306, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the compound of Example 722 (0.5 g, 1.05 mmol) in tetrahydrofuran (20 mL) was treated with triethyl amine (0.3 mL, 2.1 mmol) and acetoxy acetylchloride (0.12 mL, 1.15 mmol). After stirring at room temperature for 2 h, the reaction was complete. The reaction mixture was poured into saturated aqueous ammonium chloride. The solids were filtered off and were washed with water and diethyl ether. Title product was isolated as a white solid (0.32 g, 58%). 1H NMR (400 MHz, CD3OD) δ 7.65 (m, 3H), 7.32 (t, J=8.4 Hz, 1H), 7.04 (t, J=8.4 Hz, 2H), 6.64 (s, 1H), 5.35 (s, 2H), 4.68 (s, 2H), 2.15 (s, 3H), 2.10 (s, 3H) ppm. 19F NMR (400 MHz, CD3OD) δ−111.56 (1F), −115.99 (1F), −129.48 (1F) ppm. LC/MS, tr=5.35 minutes (5 to 95% acetonitrile/water over 8 minutes at 1 ml/min with detection 254 nm, at 50° C.). ES-MS m/z 540 (M+H). Step 2 Preparation of N-{3-[3-bromo-4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-4-fluorophenyl}-2-hydroxyacetamide

Workup

  1. filtrationThe solids were filtered off
  2. washwere washed with water and diethyl ether

Sources & evidence

ORD record
ord-8c8c054f3be14ffe9279558adda5aab5
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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