Hydrochloric Acid → HCID 44427075, compound

HRID 2233067Notes

Reaction equation

HRID 2233067 reaction equation
C[O:2][C:3](=[O:38])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:16]3=[CH:17][C:18]4[C:19]([CH3:28])([CH3:27])[CH2:20][CH2:21][C:22]([CH3:26])([CH3:25])[C:23]=4[CH:24]=[C:15]3[N:14]([CH3:29])[C:13]3[CH:30]=[CH:31][C:32]([C:34](=[O:36])[CH3:35])=[CH:33][C:12]=3[N:11]=2)=[C:6]([F:37])[CH:5]=1.C1COCC1.[OH-].[Na+].Cl>CO>[C:34]([C:32]1[CH:31]=[CH:30][C:13]2[N:14]([CH3:29])[C:15]3[C:16]([C:10]([C:7]4[CH:8]=[CH:9][C:4]([C:3]([OH:38])=[O:2])=[CH:5][C:6]=4[F:37])=[N:11][C:12]=2[CH:33]=1)=[CH:17][C:18]1[C:19]([CH3:28])([CH3:27])[CH2:20][CH2:21][C:22]([CH3:25])([CH3:26])[C:23]=1[CH:24]=3)(=[O:36])[CH3:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68465272HCID 68465272, compound

Product 1

HCID 44427075HCID 44427075, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(2-acetyl-5,7,7,10,10-pentamethyl-7,8,9,10-tetrahydro-5H-5,13-diazabenzo[4,5]cyclohepta[1,2-b]naphthalen-12-yl)-3-fluorobenzoic acid methyl ester (19) (R4=CH3, Z=3-F, 0.25 mmol) in the mixture of THF (2.5 mL) and MeOH (0.14 mL) is treated with 1N NaOH (0.41 mL) and the mixture is stirred for 12 h. The mixture is poured into 1N HCl and extracted with EtOAc. The extract is washed with brine, dried over MgSO4 and evaporated in vacuo. The resulting solids are collected by filtration and washed with Et2O to give the acid (20) (R4=CH3, Z=3-F) as yellow solid: 1H-NMR (DMSO-d6) δ: 1.00 (6H, s), 1.26 (6H, s), 1.53-1.62 (4H, m), 2.55 (3H, s), 3.29 (3H, s), 6.75 (1H, s), 7.03 (1H, s), 7.18 (1H, d), 7.71 (1H, d), 7.75 (1H, d), 7.81 (1H, dd), 7.90-7.98 (2H, m), 13.47 (1H, br).

Workup

  1. extractionextracted with EtOAc
  2. washThe extract is washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. filtrationThe resulting solids are collected by filtration
  6. washwashed with Et2O

Sources & evidence

ORD record
ord-a19e747035c4430e985b5c0d30959a52
Source dataset
uspto-grants-2010_05
Patent number
US07709470B2

Reaction notes

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