Triethylamine → HCID 11989988, compound

HRID 1715279Notes

Reaction equation

HRID 1715279 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].CC1(C)[O:24][CH:23]([CH2:25][NH2:26])[CH2:22][O:21]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]([NH:26][CH2:25][CH:23]([OH:24])[CH2:22][OH: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 41223491,3-Dioxolane-4-methanamine, 2,2-dimethyl-HCID 86621993HCID 86621993, compound

Product 1

HCID 11989988HCID 11989988, 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). 2,2-Dimethyl-1,3-dioxolane-4-methanamine (Aldrich) (0.07 ml; 0.53 mmol; 1 eq.) and triethylamine (0.15 ml; 1.06 mmol; 2 eq.) are added and the mixture is stirred overnight at rt. Solvents are evaporated and the crude product is purified by preparative HPLC. As some TFA is used for the mobile phase of the preparative HPLC, the diol protecting group is removed during the concentration of the chromatography fractions, affording directly Compound (39) as a white-off solid (26.6 mg; 14%). 1H NMR (DMSO-d6, 300 MHz) δ 2.15 (s, 3H), 2.49 (s, 3H), 3.17-3.52 (m, 4H), 3.67 (m, 1H), 4.65 (br s, 1H), 4.93 (br s, 1H), 7.99 (s, 1H), 8.46 (t, J=4.5 Hz, 1H), 12.15 (s, 1H). M− (ESI): 355.04; M+ (ESI): 356.99. HPLC (method A), Rt: 1.87 min (purity: 100%).

Workup

  1. customSolvents are evaporated
  2. customthe crude product is purified by preparative HPLC
  3. customthe diol protecting group is removed during the concentration of the chromatography fractions

Sources & evidence

ORD record
ord-c7608301daba485ba3f373804e8ac739
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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