Hydrochloric Acid → HCID 58551479, compound

HRID 2204119Notes

Reaction equation

HRID 2204119 reaction equation
[NH2:1][CH:2]1[C:11]2([CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)[O:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=O.[C:25](Cl)(=O)[CH3:26].C(N(CC)CC)C.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:45])=CC=1.Cl.O1CCOCC1>ClCCl.C1(C)C=CC=CC=1>[CH3:26][C:25]1[S:45][C:3]2[C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=3[O:10][C:11]3([CH2:12][CH2:13][NH:14][CH2:15][CH2:16]3)[C:2]=2[N:1]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 87949Lawesson's reagentHCID 58551093HCID 58551093, compound

Product 1

HCID 58551479HCID 58551479, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent3×

Procedure

tert-Butyl 3-amino-4-oxo-spiro[chromane-2,4′-piperidine]-1′-carboxylate (33 mg, 0.10 mmol), acetyl chloride (7.8 μL, 0.11 mmol), and N,N-diethylethanamine (28 μL, 0.20 mmol) were combined in dichloromethane and stirred for 30 minutes. The reaction mixture was diluted with dichloromethane and was washed with 1N HCl, a saturated solution of NaHCO3, and brine. The organics were dried over sodium sulfate and evaporated to dryness. The residue was stirred in toluene with Lawesson's reagent (40 mg, 0.10 mmol) at 70° C. overnight. The reaction was diluted with dichloromethane and filtered through a pad of Celite. The filtrate was evaporated and stirred with HCl in dioxane (1.0 mL of 4.0 M, 4.0 mmol) for 1 h at room temperature. The reaction mixture was evaporated to dryness to yield 2-methylspiro[chromeno[3,4-d]thiazole-4,4′-piperidine] (27 mg, 20%). ESI-MS m/z calc. 272.4, found 273.1 (M+1)+; Retention time: 1.05 minutes (3 min run).

Workup

  1. washwas washed with 1N HCl
  2. dry with materialThe organics were dried over sodium sulfate
  3. customevaporated to dryness
  4. filtrationfiltered through a pad of Celite
  5. customThe filtrate was evaporated
  6. customThe reaction mixture was evaporated to dryness

Sources & evidence

ORD record
ord-3f19b0bcfbd64041b7dab060490db2d2
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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