Hydrochloric Acid → HCID 58381011, compound

HRID 45215Notes

Reaction equation

HRID 45215 reaction equation
Cl.C([O:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:21][CH:22]3[CH2:27][CH2:26][CH:25]([CH:28]([NH2:37])[C:29]4[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=4)[CH2:24][CH2:23]3)=[C:17]([Cl:20])[CH:18]=2)[CH:13]=[CH:12][N:11]=1)C1C=CC=CC=1.C(#N)C.O>C(O)(C)C>[NH2:37][CH:28]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[CH:25]1[CH2:24][CH2:23][CH:22]([O:21][C:16]2[CH:15]=[C:14]3[C:19](=[CH:18][C:17]=2[Cl:20])[C:10](=[O:9])[NH:11][CH:12]=[CH:13]3)[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 18373917Acetonitrile--water (1/1)HCID 58380946HCID 58380946, compound

Product 1

HCID 58381011HCID 58381011, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A 2M aqueous solution of hydrochloric acid (3.8 mL) was added to a solution of C-[4-(1-benzyloxy-7-chloro-isoquinolin-6-yloxy)-cyclohexyl]-C-(4-methoxy-phenyl)-methylamine (36, 40 mg, 0.08 mmol) in isopropanol (4 mL). The reaction mixture was stirred overnight. Isopropanol was removed under reduced pressure and the remaining aqueous solution freeze dried to give crude product as an amorphous powder. This was treated twice with acetonitrile/water and freeze dried to give the desired product as a colourless hydrochloride salt. The relative stereochemistry was not assigned.

Workup

  1. customIsopropanol was removed under reduced pressure
  2. customthe remaining aqueous solution freeze dried
  3. customto give crude product as an amorphous powder
  4. customdried

Sources & evidence

ORD record
ord-c710b3afc3ce4e46aeea071039805522
Source dataset
uspto-grants-2013_09
Patent number
US08541449B2

Reaction notes

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