Tetrahydrofuran → HCID 86683412, compound

HRID 579435Notes

Reaction equation

HRID 579435 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.C([N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])C.[Br:13][C:14]1[S:15][C:16]([C:19]([OH:21])=O)=[CH:17][N:18]=1.[OH:22]N1C2C=CC=CC=2N=N1.Cl.C(N=C=N[CH2:38][CH2:39][CH2:40]N(C)C)C>>[Br:13][C:14]1[S:15][C:16]([C:19]([N:8]2[CH2:9][CH2:10][C:40]3[C:39]([CH:38]=[O:22])=[C:2]([O:1][CH3:5])[CH:3]=[CH:4][C:12]=3[CH2:11]2)=[O:21])=[CH:17][N:18]=1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27632102-Bromothiazole-5-carboxylic acid

Product 1

HCID 86683412HCID 86683412, compoundYield 53%

Procedure

To a mixture of dry tetrahydrofuran (20 mL) 6-Methoxy-1,2,3,4-tetrahydro-isoquinoline-5-carbaldehyde hydrochloride (683 mg, 3.00 mmol), and triethylamine (2.1 mL, 1.52 g, 15 mmol), 2-bromothiazole-5-carboxylic acid (655 mg, 3.15 mmol), 1-hydroxybenzotriazole (446 mg, 3.30 mmol) and 1-ethyl-(3-dimethylaminopropyl)-carbodiimide hydrochloride (634 mg, 3.30 mmol) were added sequentially. The mixture was stirred at room temperature for 2 h and the resulted yellow suspension was evaporated and partitioned between chloroform (30 mL) and 0.1N HCl (15 mL). The organic layer was separated and washed with saturated sodium bicarbonate (15 mL) and brine (15 mL). The organic phase was dried, evaporated and purified by column chromatography (Kieselgel 60), with chloroform as the eluent. The title compound (600 mg, 1.57 mmol, 53%) was isolated as a solid.

Workup

  1. additionwere added sequentially
  2. customthe resulted yellow suspension was evaporated
  3. custompartitioned between chloroform (30 mL) and 0.1N HCl (15 mL)
  4. customThe organic layer was separated
  5. washwashed with saturated sodium bicarbonate (15 mL) and brine (15 mL)
  6. customThe organic phase was dried
  7. customevaporated
  8. custompurified by column chromatography (Kieselgel 60), with chloroform as the eluent

Sources & evidence

ORD record
ord-93816872be66434ebd241631f661cc97
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Reaction notes

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