Triethylamine → HCID 11990110, compound

HRID 1715288Notes

Reaction equation

HRID 1715288 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[N:12]=[C:13]([C:16](Cl)=[O:17])[S:14][CH:15]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].[F:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(N(CC)CC)C>C1COCC1.C(Cl)Cl>[F:19][CH:20]1[CH2:25][CH2:24][N:23]([C:16]([C:13]2[S:14][CH:15]=[C:11]([C:7]3[S:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:9][C:8]=3[CH3:10])[N:12]=2)=[O:17])[CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27591594-FluoropiperidineHCID 86621993HCID 86621993, compound

Product 1

HCID 11990110HCID 11990110, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2′-Acetylamino-4′-methyl-[4,5′]bithiazolyl-2-carbonyl chloride, prepared as in Step I of Example 13, described above (200 mg, 0.66 mmol, 1 eq.), is dissolved in THF (8 ml) and DCM (4 ml). 4-Fluoropyperidine (Flrochem) (95.7 mg; 0.92 mmol; 1.40 eq.) and triethylamine (0.37 ml; 2.65 mmol; 4 eq.) are added and the mixture is stirred overnight at rt. Solvents are evaporated and the crude product is purified by preparative HPLC, affording Compound (48) as a white-off powder (36 mg; 13%). 1H NMR (DMSO-d6, 300 MHz) δ 1.71-2.12 (m, 4H), 2.16 (s, 3H), 2.50 (s, 3H), 3.75 (m, 2H), 4.33 (m, 2H), 4.97 (ttd, J=3, 6, 51 Hz, 1H, —CFH), 8.02 (s, 1H), 12.19 (s, 1H). M− (ESI): 367.13; M+ (ESI): 369.12. HPLC (method A), Rt: 3.04 min (purity: 95.8%).

Workup

  1. customSolvents are evaporated
  2. customthe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-99b63618ab45437f8c00e85204604fd9
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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