Hydrochloric Acid → HCID 9887654, compound

HRID 1057494Notes

Reaction equation

HRID 1057494 reaction equation
C[O:2][C:3](=[O:38])[CH2:4][CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][N:8]([C:16](=[O:37])[CH2:17][CH2:18][CH2:19][C:20]2[N:25]=[C:24]3[N:26](C(OC(C)(C)C)=O)[CH2:27][CH2:28][CH2:29][C:23]3=[CH:22][CH:21]=2)[CH2:7][CH2:6]1.Cl.O1CCOCC1.[OH-].[Na+].Cl>>[NH:26]1[C:24]2=[N:25][C:20]([CH2:19][CH2:18][CH2:17][C:16]([N:8]3[CH2:9][C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[CH:5]([CH2:4][C:3]([OH:38])=[O:2])[CH2:6][CH2:7]3)=[O:37])=[CH:21][CH:22]=[C:23]2[CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 204431481,4-Dioxane hydrochlorideHCID 86758820HCID 86758820, compound

Product 1

HCID 9887654HCID 9887654, compound

Procedure

To methyl-2-[2-(4-{1-[(tert-butyl)oxycarbonyl]-1,2,3,4-tetrahydropyridino[2,3-b]pyridin-7-yl}butanoyl)-1H,3H,4H,5H-benzo[e]azepin-5-yl]acetate was added 4.0M HCl/dioxane (4 mL) and the resulting mixture was stirred for 18 hrs at room temperature, concentrated by rotary evaporation, diluted in MeOH followed by the addition of 1N NaOH (5 eq). The mixture was stirred at room temperature for 48 hrs., acidified with 1N HCl, concentrated by rotary evaporation and extracted with dichloromethane. The organic solvent was concentrated concentrated in vacuo to afford the desired product. EI-MS m/z 408 (M+H)+. 1H-NMR (400MHz, CDCl3): δ7.3-7.1 (m, 4H), 6.35 (m, 2H), 4.75 (d, J=15.1, 1H), 4.55 (m, 2H), 3.8 (m, 1H), 3.5 (m, 5H), 2.4 (m, 3H), 2.15 (m,2H), 2.0 (m,3H), 1.9 (m, 3H), 1.7 (m, 1H).

Workup

  1. concentrationconcentrated by rotary evaporation
  2. additiondiluted in MeOH
  3. stirringThe mixture was stirred at room temperature for 48 hrs
  4. concentrationconcentrated by rotary evaporation
  5. extractionextracted with dichloromethane
  6. concentrationThe organic solvent was concentrated
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d0d7b116e9b5439297daf8e26a510cce
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

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