Triethylamine → HCID 11989861, compound

HRID 1715270Notes

Reaction equation

HRID 1715270 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].[OH:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(N(CC)CC)C>C1COCC1.C(Cl)Cl>[OH: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 79341Piperidin-4-olHCID 86621993HCID 86621993, compound

Product 1

HCID 11989861HCID 11989861, compoundYield 40%

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, (166.6 mg, 0.55 mmol, 1 eq.), is dissolved in THF (8 ml) and DCM (4 ml). 4-Hydroxypiperidine (Fluka)(55.8 mg; 0.55 mmol; 1 eq.) and triethylamine (0.15 ml; 1.10 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 (29) as a brown solid (80.3 mg; 40%). 1H NMR (DMSO-d6, 300 MHz) δ 1.44 (m, 2H), 1.82 (m, 2H), 2.14 (s, 3H), 2.50 (s, 3H), 3.35 (m, 2H), 3.80 (m, 2H), 4 (m, 1H), 4.60 (m, 1H), 7.98 (s, 1H), 12.16 (br s, 1H). M− (ESI): 365; M+ (ESI): 367. HPLC (method A), Rt: 2.31 min (purity: 91.1%).

Workup

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

Sources & evidence

ORD record
ord-47b60781593c4a49ab5dbb561ad39892
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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