Triethylamine → HCID 11990106, compound

HRID 1715284Notes

Reaction equation

HRID 1715284 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].[CH2:19]([NH2:22])[C:20]#[CH:21].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]([NH:22][CH2:19][C:20]#[CH:21])=[O:17])[S:14][CH:15]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 239041PropargylamineHCID 86621993HCID 86621993, compound

Product 1

HCID 11990106HCID 11990106, compoundYield 49%

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). Propargylamine (Fluka) (35.0 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 (44) as a pale yellow powder (83.3 mg; 49%). 1H NMR (DMSO-d6, 300 MHz) δ 2.14 (s, 3H), 2.49 (s, 3H), 3.14 (s, 1H, C—CH), 4.04 (m, 2H), 8.01 (s, 1H), 9.20 (t, J=4.5 Hz, 1H), 12.15 (s, 1H). M− (ESI): 319.05; M+ (ESI): 321.05. HPLC (method A), Rt: 2.71 min (purity: 100%).

Workup

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

Sources & evidence

ORD record
ord-44a6d92305ec405596124737dfa2ca66
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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