Hydrochloric Acid → HCID 131724528, compound

HRID 1836562Notes

Reaction equation

HRID 1836562 reaction equation
[ClH:1].[CH:2]1[CH:11]=[CH:10][C:9]2[CH2:12][CH2:13][CH2:14][N:7]3[C:8]=2[C:3]=1[C@@H:4]1[CH2:18][NH:17][CH2:16][C@H:5]1[C:6]3=[O:15].C=O.[C:21](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>ClCCCl.C(O)C.CCOCC>[ClH:1].[CH3:21][N:17]1[CH2:18][C@@H:4]2[C@H:5]([C:6](=[O:15])[N:7]3[CH2:14][CH2:13][CH2:12][C:9]4[CH:10]=[CH:11][CH:2]=[C:3]2[C:8]3=4)[CH2:16]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 131724527HCID 131724527, compound

Product 1

HCID 131724528HCID 131724528, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of (±)-trans-5,6,9,10,11,11a-hexahydro-4H-pyrido[3,2,1-ij]pyrrolo[3,4-c]quinolin-8(8aH)-one, hydrochloride salt from EXAMPLE 3 (200 mg, 0.76 mmol) in 5 mL of 1,2-dichloroethane was added 37% aqueous formaldehyde (0.065 mL, 0.76 mmol) and sodium triacetoxyborohydride (260 mg, 1.22 mmol). The resulting mixture was stirred at ambient temperature for 1 h and then the reaction was quenched with water. The mixture was partitioned between chloroform and saturated aqueous sodium carbonate. The organics were washed with brine, dried (K2CO3) and concentrated in vacuo. A portion of the residue (50 mg, 0.21 mmol) was dissolved in 1 mL ethanol and 5 mL of ether and then there was added 2M HCl in ether (0.105 mL, 0.21 mmol). A solid precipitated out of solution. The solvents were decanted and the solid was triturated twice with ether and dried in vacuo to afford 25 mg (43%) of the title compound of EXAMPLE 5 as an off white powder. 1H NMR (d6-dmso): δ 7.12 (d, 1H, J=7.4 Hz), 6.99 (t, 1H, J=7.3 Hz), 6.97-6.90 (m, 1H), 4.25-4.12 (m, 2H), 3.75-3.65 (m, 2H), 3.40-3.20 (m, 3H), 2.97-2.90 (m, 3H), 22.81-2.70 (m, 3H), 1.88-1.80 (m, 2H). LRMS (ES)+: 243.4 (M+H)+.

Workup

  1. customthe reaction was quenched with water
  2. customThe mixture was partitioned between chloroform and saturated aqueous sodium carbonate
  3. washThe organics were washed with brine
  4. dry with materialdried (K2CO3)
  5. concentrationconcentrated in vacuo
  6. customA solid precipitated out of solution
  7. customThe solvents were decanted
  8. customthe solid was triturated twice with ether
  9. customdried in vacuo

Sources & evidence

ORD record
ord-7649af5ba19749379feeda3682bd349c
Source dataset
uspto-grants-2004_08
Patent number
US06777406B2

Reaction notes

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