Diisopropylethylamine → Thiazole-5-carboxylic acid {(S)-1-[4-(5-methoxy-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-phenyl]-ethyl}-amide

HRID 524017Notes

Reaction equation

HRID 524017 reaction equation
[S:1]1[C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=[CH:2]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.[CH3:41][O:42][C:43]1[CH:52]=[CH:51][CH:50]=[C:49]2[C:44]=1[CH2:45][CH2:46][N:47]([CH2:53][C:54]1[CH:59]=[CH:58][C:57]([C@@H:60]([NH2:62])[CH3:61])=[CH:56][CH:55]=1)[CH2:48]2>CN(C=O)C>[CH3:41][O:42][C:43]1[CH:52]=[CH:51][CH:50]=[C:49]2[C:44]=1[CH2:45][CH2:46][N:47]([CH2:53][C:54]1[CH:55]=[CH:56][C:57]([C@@H:60]([NH:62][C:6]([C:5]3[S:1][CH:2]=[N:3][CH:4]=3)=[O:8])[CH3:61])=[CH:58][CH:59]=1)[CH2:48]2

Participants

6

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 84494Thiazole-5-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 118939145(S)-1-[4-(5-methoxy-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-phenyl]-ethylamine hydrochloride

Product 1

HCID 118940320Thiazole-5-carboxylic acid {(S)-1-[4-(5-methoxy-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-phenyl]-ethyl}-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

37 mg (0.29 mmol) Thiazole-5-carboxylic acid, 83 μl (0.48 mmol) DIPEA and 154 mg (0.481 mmol) TBTU in 0.5 mL DMF are stirred for 10 min at r.t. Then 80 mg (0.24 mmol) (S)-1-[4-(5-methoxy-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-phenyl]-ethylamine hydrochloride (example XXXIII.2) in 1.0 mL DMF and 102 μl (0.601 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-919344d79e4f4b58b33611b6e2031b26
Source dataset
uspto-grants-2016_05
Patent number
US09340510B2

Reaction notes

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