Hydroxyamine hydrochloride → HCID 178521731, compound

HRID 1028216Notes

Reaction equation

HRID 1028216 reaction equation
C([O:3][C:4]([CH2:6][C:7](=[O:39])[CH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([O:15][C:16]([N:18]2[CH2:27][CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[C:23]([NH:28][C:29]([NH:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=4[F:38])=[O:30])[CH:24]=3)[CH2:19]2)=[O:17])[CH2:11][CH2:10]1)=O)C.Cl.[NH2:41]O>C(O)C>[OH:3][C:4]1[CH:6]=[C:7]([CH2:8][C@H:9]2[CH2:10][CH2:11][C@H:12]([O:15][C:16]([N:18]3[CH2:27][CH2:26][C:25]4[C:20](=[CH:21][CH:22]=[C:23]([NH:28][C:29]([NH:31][C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=5[F:38])=[O:30])[CH:24]=4)[CH2:19]3)=[O:17])[CH2:13][CH2:14]2)[O:39][N:41]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 178472213HCID 178472213, compound

Product 1

HCID 178521731HCID 178521731, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of trans-6-[3-(2-fluoro-phenyl)-ureido]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid 4-(3-ethoxycarbonyl-2-oxo-propyl)-cyclohexyl ester (127 mg) obtained in Example (42a) and ethanol (3 mL), hydroxylamine hydrochloride (164 mg) was added at room temperature in the same way as in Example (42b). The reaction mixture was heated at 80° C. for 12 hours and concentrated. The residue was purified by column chromatography (dichloromethane/ethyl acetate). The obtained solid was purified by PTLC (dichloromethane/ethyl acetate=1:1) to obtain the title compound (34 mg, 28%) as an orange solid.

Workup

  1. additionwas added at room temperature in the same way as in Example (42b)
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography (dichloromethane/ethyl acetate)
  4. customThe obtained solid was purified by PTLC (dichloromethane/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-4f1ec79c86f7442eaeeac78ca917f7ba
Source dataset
uspto-grants-2014_05
Patent number
US08735425B2

Reaction notes

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