Triethylamine → HCID 86621998, compound

HRID 1715292Notes

Reaction equation

HRID 1715292 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].[C@H:19]12[O:28][C@H:23]([O:24][C@@H:25]1[CH2:26][OH:27])[CH2:22][NH:21][CH2:20]2.C(N(CC)CC)C>C1COCC1.C(Cl)Cl>[OH:27][CH2:26][C@@H:25]1[C@@H:19]2[O:28][C@@H:23]([CH2:22][N:21]([C:16]([C:13]3[S:14][CH:15]=[C:11]([C:7]4[S:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:9][C:8]=4[CH3:10])[N:12]=3)=[O:17])[CH2:20]2)[O:24]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 68408578HCID 68408578, compoundHCID 86621993HCID 86621993, compound

Product 1

HCID 86621998HCID 86621998, 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 (200 mg, 0.66 mmol, 1 eq.), is dissolved in THF (8 ml) and DCM (4 ml). (1R,5R,7R)-6,8-Dioxa-3-azabicyclo[3.2.1]oct-7-ylmethanol, synthesized according the literature (Guarna et al., 1999, J. Org. Chem., 64, 7347) (96.2 mg; 0.66 mmol; 1 eq.), and triethylamine (0.37 ml; 2.65 mmol; 4 eq.) are added and the mixture is stirred 1 hour at rt. Solvents are evaporated and the crude product is purified by preparative HPLC, affording Compound (51) as a white-off powder (110 mg; 40%). M− (ESI): 408.99; M+ (ESI): 410.89. HPLC (method A), Rt: 2.15 min (purity: 99.8%).

Workup

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

Sources & evidence

ORD record
ord-b91b93f09bbf4866ba271c3a54b8720c
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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