Triethylamine → HCID 11989987, compound

HRID 1715278Notes

Reaction equation

HRID 1715278 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].[O:19]1[C:23]2([CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[O:22][CH2:21][CH2:20]1.C(N(CC)CC)C>C1COCC1.C(Cl)Cl>[O:19]1[C:23]2([CH2:28][CH2:27][N:26]([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])[CH2:25][CH2:24]2)[O:22][CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 86621993HCID 86621993, compound

Product 1

HCID 11989987HCID 11989987, compoundYield 30%

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). 1,4-Dioxa-8-azaspiro[4.5]decane (Aldrich) (0.06 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 precipitation in MeOH, affording Compound (38) as a beige solid (64.9 mg, 30%). 1H NMR (DMSO-d6, 300 MHz) δ 1.73 (m, 4H), 2.13 (s, 3H), 2.48 (s, 3H), 3.72 (m, 2H), 3.93 (m, 4H), 4.28 (m, 2H), 7.99 (s, 1H), 12.16 (s, 1H). M− (ESI): 407.10; M+ (ESI): 409.21. HPLC (method A), Rt: 2.86 min (purity: 94%).

Workup

  1. customSolvents are evaporated
  2. customthe crude product is purified by precipitation in MeOH

Sources & evidence

ORD record
ord-bc15174608f24e65a5c2de220a31a022
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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