Hydrochloric Acid → HCID 58136535, compound

HRID 877177Notes

Reaction equation

HRID 877177 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[N:10]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([CH:26]([CH:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)[C:27](O)=[O:28])=[CH:22][CH:21]=3)[N:9]=2)=[CH:4][CH:3]=1.Cl.[NH2:36][CH2:37][C:38]1[CH:43]=[CH:42][C:41]([C:44]([O:46][CH3:47])=[O:45])=[CH:40][CH:39]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.Cl>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[N:10]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([CH:26]([CH:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)[C:27]([NH:36][CH2:37][C:38]4[CH:39]=[CH:40][C:41]([C:44]([O:46][CH3:47])=[O:45])=[CH:42][CH:43]=4)=[O:28])=[CH:24][CH:25]=3)[N:9]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2729253Methyl 4-(aminomethyl)benzoate hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 58136554HCID 58136554, compound

Product 1

HCID 58136535HCID 58136535, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

60 mg (0.127 mmol) of (4-{[4-(4-chlorophenyl)-1-oxophthalazin-2(1H)-yl]methyl}phenyl)(cyclopentyl)acetic acid (Example 65A) were dissolved in 0.6 ml of dichloromethane, and 26 mg (0.127 mmol) of methyl 4-(aminomethyl)benzenecarboxylate hydrochloride, 19 mg (0.140 mmol) of 1-hydroxy-1H-benzotriazole hydrate, 28 mg (0.146 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 28 mg (0.273 mmol) of triethylamine were added in succession. The reaction mixture was stirred at room temperature overnight. 1 N hydrochloric acid was then added, and the mixture was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated on a rotary evaporator. The residue was purified by preparative HPLC. This gave 36 mg (46% of theory) of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. concentrationconcentrated on a rotary evaporator
  4. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-465a74a2e73e4955bde7ad01865ba892
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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