Triethylamine → HCID 11990105, compound

HRID 1715283Notes

Reaction equation

HRID 1715283 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[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20]1.C(N(CC)CC)C>C1COCC1.C(Cl)Cl>[OH:24][CH:21]1[CH2:22][CH2:23][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]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 982104-HydroxypyrrolidineHCID 86621993HCID 86621993, compound

Product 1

HCID 11990105HCID 11990105, 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 (160 mg, 0.53 mmol, 1 eq.), is dissolved in THF (8 ml) and DCM (4 ml). 3-Pyrrolidinol (Fluka) (55.4 mg; 0.64 mmol; 1.20 eq.) and triethylamine (0.22 ml; 1.59 mmol; 3 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 (43) as a white-off powder (40.1 mg; 21.5%). 1H NMR (DMSO-d6, 300 MHz) δ 1.75-2.12 (m, 3H), 2.12 (s, 3H), 2.48 (s, 3H), 3.45-3.70 (m, 2H), 3.90-4.25 (m, 2H), 4.31-4.40 (m, 1H), 7.97 (s, 1H), 12.13 (s, 1H). M− (ESI): 353.07; M+ (ESI): 351.09. HPLC(method A), Rt: 2.21 min (purity: 99.3%).

Workup

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

Sources & evidence

ORD record
ord-5bb3ee6275654ebc9faa0a236082b180
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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