Diisopropylethylamine → HCID 71550253, compound

HRID 1054139Notes

Reaction equation

HRID 1054139 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:38]2[CH:42]=[N:41][N:40]=[N:39]2)=[C:6](/[CH:8]=[CH:9]/[C:10]([N:12]2[C@H:21]([C:22]([NH:24][C:25]3[CH:37]=[CH:36][C:28]([C:29]([O:31]C(C)(C)C)=[O:30])=[CH:27][CH:26]=3)=[O:23])[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13]2)=[O:11])[CH:7]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:38]2[CH:42]=[N:41][N:40]=[N:39]2)=[C:6](/[CH:8]=[CH:9]/[C:10]([N:12]2[C@H:21]([C:22]([NH:24][C:25]3[CH:26]=[CH:27][C:28]([C:29]([OH:31])=[O:30])=[CH:36][CH:37]=3)=[O:23])[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13]2)=[O:11])[CH:7]=1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 131733302HCID 131733302, compound

Product 1

HCID 71550253HCID 71550253, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S,E)-tert-Butyl 4-(2-(3-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)acryloyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamido)benzoate: To 1B (0.1 g, 0.284 mmol) and Intermediate 1 (0.099 g, 0.284 mmol) in DMF (2 ml) was added DIEA (0.149 ml, 0.851 mmol). The reaction was quenched with H2O (10 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were washed with H2O (10 mL), brine (10 mL) and dried (MgSO4). Purified by normal phase chromatography to afford 0.15 g of desired product as yellow solid. MS (ESI) m/z: 585.2 (M+H)+. (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 H2O (10 mL), brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. customPurified by normal phase chromatography

Sources & evidence

ORD record
ord-22249e0032e842c7ab6bece7de4dc963
Source dataset
uspto-grants-2016_07
Patent number
US09394276B2

Reaction notes

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