Triethylamine → HCID 21035306, compound

HRID 1867185Notes

Reaction equation

HRID 1867185 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[CH:5][C:6]([F:28])=[C:7]([N:9]2[C:14]([CH3:15])=[CH:13][C:12]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[F:25])=[C:11]([Br:26])[C:10]2=[O:27])[CH:8]=1.C(N(CC)CC)C.[C:36]([O:39][CH2:40][C:41](Cl)=[O:42])(=[O:38])[CH3:37].[Cl-].[NH4+]>O1CCCC1>[C:36]([O:39][CH2:40][C:41]([NH:2][C:3]1[CH:4]=[CH:5][C:6]([F:28])=[C:7]([N:9]2[C:14]([CH3:15])=[CH:13][C:12]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[F:25])=[C:11]([Br:26])[C:10]2=[O:27])[CH:8]=1)=[O:42])(=[O:38])[CH3:37]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 26297Acetoxyacetyl chlorideHCID 22050202HCID 22050202, 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).

Workup

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

Sources & evidence

ORD record
ord-4b90570aaa6846ff969a9a679daad645
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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