Hydrochloric Acid → HCID 86713680, compound

HRID 1430543Notes

Reaction equation

HRID 1430543 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:11])=[CH:4][C:3]=1[C:19]1[C:20](=[O:39])[N:21]([CH2:37][CH3:38])[C:22]2[C:27]([CH:28]=1)=[CH:26][N:25]=[C:24]([NH:29][C:30]([C@@H:32]1[CH2:36][CH2:35][CH2:34][NH:33]1)=[O:31])[CH:23]=2.[ClH:40].CC(OC)(C)C>CC#N>[ClH:1].[ClH:40].[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([NH:9][C:10]([NH:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:11])=[CH:4][C:3]=1[C:19]1[C:20](=[O:39])[N:21]([CH2:37][CH3:38])[C:22]2[C:27]([CH:28]=1)=[CH:26][N:25]=[C:24]([NH:29][C:30]([C@@H:32]1[CH2:36][CH2:35][CH2:34][NH:33]1)=[O:31])[CH:23]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15413tert-Butyl methyl etherHCID 71584756HCID 71584756, compound

Product 1

HCID 86713680HCID 86713680, compoundYield 127.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (S)—N-(3-(2-chloro-4-fluoro-5-(3-phenylureido)phenyl)-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl)pyrrolidine-2-carboxamide (43 mg, 0.078 mmol) in MeCN (3 mL) was treated with 0.1N HCl (aq.) (1.56 mL, 0.156 mmol), frozen and lyophilized. The material was treated with MTBE, sonicated, the solid collected via filtration and dried to afford (S)—N-(3-(2-chloro-4-fluoro-5-(3-phenylureido)phenyl)-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl)pyrrolidine-2-carboxamide dihydrochloride (31 mg, 63% yield). MS (ESI) m/z: 549.2 [M+H]+.

Workup

  1. temperaturefrozen
  2. customsonicated
  3. filtrationthe solid collected via filtration
  4. customdried

Sources & evidence

ORD record
ord-17086d7e439f4d8a8028d231be3ff2df
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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