2-Methoxyethylamine → HCID 89510331, compound

HRID 1525367Notes

Reaction equation

HRID 1525367 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:45]2[CH:49]=[N:48][N:47]=[N:46]2)=[C:6](/[CH:8]=[CH:9]/[C:10]([N:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[C:22](=[O:28])[NH:23][CH2:24][CH2:25][O:26][CH3:27])[CH:13]2[C:29]([NH:31][C:32]2[CH:44]=[CH:43][C:35]([C:36]([O:38]C(C)(C)C)=[O:37])=[CH:34][CH:33]=2)=[O:30])=[O:11])[CH:7]=1.COCCN.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:45]2[CH:49]=[N:48][N:47]=[N:46]2)=[C:6](/[CH:8]=[CH:9]/[C:10]([N:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[C:22](=[O:28])[NH:23][CH2:24][CH2:25][O:26][CH3:27])[CH:13]2[C:29]([NH:31][C:32]2[CH:33]=[CH:34][C:35]([C:36]([OH:38])=[O:37])=[CH:43][CH:44]=2)=[O:30])=[O:11])[CH:7]=1

Participants

6

Reactant 4

HCID 80182-MethoxyethylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 131733150HCID 131733150, compound

Product 1

HCID 89510331HCID 89510331, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(E)-tert-Butyl 4-(2-(3-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)acryloyl)-5-(2-methoxyethylcarbamoyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxamido)benzoate: To 3A (46 mg, 0.073 mmol), 2-methoxyethanamine (5.49 mg, 0.073 mmol), BOP (32.3 mg, 0.073 mmol) in DMF (1 mL) was added DIEA (12.77 μL, 0.073 mmol). After 24 h, the reaction was quenched with H2O (10 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were washed with brine (10 mL) and dried (MgSO4). MS (ESI) m/z: 686.0 (M+H)+.

Workup

  1. customthe reaction was quenched with H2O (10 mL)
  2. extractionextracted with EtOAc (3×20 mL)
  3. washThe combined organic layers were washed with brine (10 mL)
  4. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-0d107f98066d4dc0b52fb5381e438896
Source dataset
uspto-grants-2015_07
Patent number
US09079929B2

Reaction notes

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