Hydrochloric Acid → 7-[(3R)-3-Amino-4-(2,5-difluorophenyl)butanoyl]-N-(tert-butyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydro-1,7-naphthyridine-3-carboxamide, hydrochloride

HRID 132883Notes

Reaction equation

HRID 132883 reaction equation
C(OC([NH:8][C@H:9]([CH2:34][C:35]1[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:36]=1[F:42])[CH2:10][C:11]([N:13]1[CH2:22][C:21]2[N:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[C:18]([C:27]([NH:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:17][C:16]=2[CH2:15][CH2:14]1)=[O:12])=O)(C)(C)C.CO.[ClH:45]>O1CCOCC1>[ClH:45].[NH2:8][C@H:9]([CH2:34][C:35]1[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:36]=1[F:42])[CH2:10][C:11]([N:13]1[CH2:22][C:21]2[N:20]=[C:19]([C:23]([F:26])([F:24])[F:25])[C:18]([C:27]([NH:29][C:30]([CH3:32])([CH3:33])[CH3:31])=[O:28])=[CH:17][C:16]=2[CH2:15][CH2:14]1)=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 692236217-[(3r)-3-[(Tert-butoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoyl]-n-(tert-butyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydro-1,7-naphthyridine-3-carboxamide

Product 1

HCID 1317269347-[(3R)-3-Amino-4-(2,5-difluorophenyl)butanoyl]-N-(tert-butyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydro-1,7-naphthyridine-3-carboxamide, hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of the product (25 mg) from Step A above, 0.5 mL of methanol and 2.5 mL of 4.0M hydrogen chloride in 1,4-dioxane was kept at room temperature for 18 h. The volatiles were removed under a stream of nitrogen, and the residue was triturated with ether. The resultant precipitate was collected and dried in vacuo to afford the title compound as a white powder. LC/MS: 499.1 (M+1).

Workup

  1. customThe volatiles were removed under a stream of nitrogen
  2. customthe residue was triturated with ether
  3. customThe resultant precipitate was collected
  4. customdried in vacuo

Sources & evidence

ORD record
ord-d0fd6093702b4b0a9554dfca04347752
Source dataset
uspto-grants-2008_06
Patent number
US07388019B2

Reaction notes

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