Triethylamine → HCID 11989860, compound

HRID 1715269Notes

Reaction equation

HRID 1715269 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].[NH:19]1[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][OH:27])[CH2:21][CH2:20]1.C(N(CC)CC)C>C1COCC1.C(Cl)Cl>[OH:27][CH2:26][CH2:25][CH:22]1[CH2:23][CH2:24][N:19]([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])[CH2:20][CH2:21]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 739534-PiperidineethanolHCID 86621993HCID 86621993, compound

Product 1

HCID 11989860HCID 11989860, compoundYield 43%

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-Piperidineethanol (Aldrich)(85.6 mg; 0.66 mmol; 1 eq.) and triethylamine (0.19 ml; 1.33 mmol; 2 eq.) are added and the mixture is stirred overnight at rt. Solvents are evaporated and the crude product is crystallized in MeOH, affording Compound (28) as a brown solid (117.2 mg; 43%). 1H NMR (DMSO-d6, 300 MHz) δ 1.05-1.30 (m, 2H), 1.38 (m, 2H), 1.75 (m, 2H), 2.13 (s, 3H), 2.48 (s, 3H), 2.85 (m, 1H), 3.22 (m, 1H), 3.45 (m, 2H), 4.38 (t, J=6 Hz, 1H), 4.42 (m, 1H), 5.15 (m, 1H), 7.97 (s, 1H), 12.16 (s, 1H). M− (ESI): 393.21; M+ (ESI): 395.20. HPLC (method A), Rt: 2.69 min (purity: 95.7%).

Workup

  1. customSolvents are evaporated
  2. customthe crude product is crystallized in MeOH

Sources & evidence

ORD record
ord-e7078221ca82496ea8556a458671b059
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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