Benzylamine → HCID 118939094, compound

HRID 524021Notes

Reaction equation

HRID 524021 reaction equation
[C:1]([NH:4][C@H:5]([C:7]1[CH:26]=[CH:25][C:10]([CH2:11][N:12]2[CH2:21][CH2:20][C:19]3[C:18]([C:22]([OH:24])=O)=[CH:17][CH:16]=[CH:15][C:14]=3[CH2:13]2)=[CH:9][CH:8]=1)[CH3:6])(=[O:3])[CH3:2].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH2:58]([NH2:65])[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1>CN(C=O)C>[CH2:58]([NH:65][C:22]([C:18]1[C:19]2[CH2:20][CH2:21][N:12]([CH2:11][C:10]3[CH:25]=[CH:26][C:7]([C@@H:5]([NH:4][C:1](=[O:3])[CH3:2])[CH3:6])=[CH:8][CH:9]=3)[CH2:13][C:14]=2[CH:15]=[CH:16][CH:17]=1)=[O:24])[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 81531Diisopropylethylamine2×HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 118939113HCID 118939113, compound

Product 1

HCID 118939094HCID 118939094, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

80 mg (0.15 mmol, 65%) 2-[4-((S)-1-Acetylamino-ethyl)-benzyl]-1,2,3,4-tetrahydro-isoquinoline-5-carboxylic acid (example XXXVII), 51 μL (0.30 mmol) DIPEA and 95 mg (0.30 mmol) TBTU in 1 mL DMF are stirred at r.t. for 10 min. Then 16 mg (0.15 mmol) benzylamine and 63 μL (0.37 mmol) DIPEA are added and the resulting mixture is stirred at r.t. for 2 h. After that time, the reaction is quenched by the addition of 200 μL water and purified by HPLC.

Workup

  1. customAfter that time, the reaction is quenched by the addition of 200 μL water
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-08a4ba81eee74570874f00f16fd27744
Source dataset
uspto-grants-2016_05
Patent number
US09340510B2

Reaction notes

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