Nipecotic Acid → HCID 11989748, compound

HRID 1715265Notes

Reaction equation

HRID 1715265 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[CH2:27][CH2:26][CH2:25][CH:21]([C:22]([OH:24])=[O:23])[CH2:20]1.C(N(CC)CC)C>C1COCC1.C(Cl)Cl>[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[N:12]=[C:13]([C:16]([N:19]3[CH2:27][CH2:26][CH2:25][CH:21]([C:22]([OH:24])=[O:23])[CH2:20]3)=[O:17])[S:14][CH:15]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 4498Nipecotic AcidHCID 8471TriethylamineHCID 86621993HCID 86621993, compound

Product 1

HCID 11989748HCID 11989748, compoundYield 23%

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, (106.5 mg; 0.35 mmol; 1 eq.), is dissolved in THF (8 ml) and DCM (4 ml). Nipecotic acid (Emkachem)(42.8 mg; 0.33 mmol; 1 eq.) and triethylamine (97 μl; 0.70 mmol; 2 eq.) are added and the mixture is stirred overnight at rt. Solvents are evaporated and the crude product is crystallized in MeOH, filtrated, affording Compound (21) as a brown solid (31 mg; 23%). M− (ESI): 393; M+ (ESI): 395. HPLC (method A), Rt: 2.60 min (purity: 95.4%).

Workup

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

Sources & evidence

ORD record
ord-6726527b578046909ddbb157da4d0d5a
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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