Ammonia → HCID 59447545, compound

HRID 1518326Notes

Reaction equation

HRID 1518326 reaction equation
Cl.Cl.[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[NH:12][C:13]([C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:24]=1[CH2:23][NH:22][CH2:21][CH2:20]2)=[O:14].[N:25]1([C:30](N2C=CN=C2)=[S:31])C=CN=C1.N>CN(C=O)C>[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[NH:12][C:13]([C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:24]=1[CH2:23][N:22]([C:30](=[S:31])[NH2:25])[CH2:21][CH2:20]2)=[O:14]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 802641,1'-ThiocarbonyldiimidazoleHCID 86644320N-(benzo[d]thiazol-2-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxamide dihydrochloride

Product 1

HCID 59447545HCID 59447545, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of compound 1B (3.25 g, 8.50 mmol) in DMF (50 mL) was added TEA (4.71 mL, 34.0 mmol). The resulting mixture was stirred for 10 minutes and di(1H-imidazol-1-yl)methanethione (1.818 g, 10.20 mmol) was added. The reaction mixture was stirred at rt for 30 minutes. Ammonia (7 N in MeOH) (48.6 mL, 340 mmol) was added and the resulting mixture was stirred overnight. The reaction mixture was concentrated to remove the ammonia and MeOH. The DMF solution was directly used for the next step without further purification. LCMS (APCI): m/z 369 (M+H).

Workup

  1. stirringThe reaction mixture was stirred at rt for 30 minutes
  2. stirringthe resulting mixture was stirred overnight
  3. concentrationThe reaction mixture was concentrated
  4. customto remove the ammonia and MeOH
  5. customThe DMF solution was directly used for the next step without further purification

Sources & evidence

ORD record
ord-cd51be4e0ad948e38314b2d5924f6fa6
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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