2-Methoxyethylamine → HCID 59536294, compound

HRID 445346Notes

Reaction equation

HRID 445346 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][N:10]2[C:19](OC2C=CC([N+]([O-])=O)=CC=2)=[O:20])=[CH:5][CH:4]=1.[CH3:33][O:34][CH2:35][CH2:36][NH2:37]>CC#N>[CH3:33][O:34][CH2:35][CH2:36][NH:37][C:19]([N:10]1[CH2:11][CH2:12][C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@H:9]1[C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:31])([F:32])[F:1])=[CH:8][CH:7]=1)=[O:20]

Participants

4

Reactant 2

HCID 80182-Methoxyethylamine2×HCID 59536297(R)-4-Nitrophenyl 1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 59536294HCID 59536294, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (R)-4-nitrophenyl 1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (170 mg, 384 μmol, example 88) in MeCN (0.2 mL) was added 2-methoxyethylamine (36.7 μL, 423 μmol). The resulting mixture was then subjected to a microwave irradiation at 180° C. for 15 min. Then, 2-methoxy-ethylamine (0.02 mL) was added and the mixture was subjected to a microwave irradiation at 180° C. for an additional 15 min. Then, the solvent was removed and the residue was dissolved in a solution of DMSO and MeOH (1:1, 1.0 mL). The solution mixture was then purified by preparative HPLC (0%-100% MeCN 0.1% TFA/H2O 0.1% TFA) to give the desired product, which was then dissolved in MeOH (2.0 mL). The solution was washed through PL-HCO3 MP resin (200 mg per 6 mL tube) and the resin was washed with MeOH (2×0.5 mL). The combined washings were then concentrated and dried under vacuum to give the title compound as a yellow solid. MS (ESI, positive ion) m/z: 379 (M+H).

Workup

  1. customThe resulting mixture was then subjected to a microwave irradiation at 180° C. for 15 min
  2. customthe mixture was subjected to a microwave irradiation at 180° C. for an additional 15 min
  3. customThen, the solvent was removed
  4. dissolutionthe residue was dissolved in a solution of DMSO and MeOH (1:1, 1.0 mL)
  5. customThe solution mixture was then purified by preparative HPLC (0%-100% MeCN 0.1% TFA/H2O 0.1% TFA)

Sources & evidence

ORD record
ord-cba8f035c2314438818fc824c65abd5e
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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