Aniline → HCID 131733149, compound

HRID 1525365Notes

Reaction equation

HRID 1525365 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:18](O)=[O:19])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.CN(C=O)C>CCOC(C)=O>[C:22]1([NH:21][C:18]([C:13]2[CH:14]=[C:15]3[C:16](=[CH:11][CH:12]=2)[CH2:17][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]3)=[O:19])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 6228DimethylformamideHCID 111923Propylphosphonic anhydrideHCID 113578872-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid

Product 1

HCID 131733149HCID 131733149, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid (0.2 g, 0.721 mmol) and aniline (0.066 mL, 0.721 mmol) and TEA (0.251 mL, 1.803 mmol) in EtOAc (5 mL) was added a 50% solution of T3P in DMF (0.408 mL, 1.442 mmol). After 24 h, the reaction was partitioned with dilute HCl (10 mL) and EtOAc (20 mL). The organic layer was washed with brine (10 mL) and dried (MgSO4). Purification by silica gel chromatography afforded 0.238 g of Intermediate 19A. MS (ESI) m/z: 352.9 (M+H)+.

Workup

  1. customthe reaction was partitioned with dilute HCl (10 mL) and EtOAc (20 mL)
  2. washThe organic layer was washed with brine (10 mL)
  3. dry with materialdried (MgSO4)
  4. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-8103bb7fe47140c8b37bfa59ff7647a8
Source dataset
uspto-grants-2015_07
Patent number
US09079929B2

Reaction notes

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