Triethylamine → HCID 67389261, compound

HRID 1929404Notes

Reaction equation

HRID 1929404 reaction equation
[CH3:1][C@@H:2]1[C@@H:7]([NH:8][CH:9]2[CH2:14][CH2:13][CH:12]([C:15]3[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)[CH2:6][C@H:5]2[CH2:26][C@@H:3]1[C:4]2([CH3:28])[CH3:27].C(N(CC)CC)C.[C:36]1([CH2:42][CH2:43][C:44](Cl)=[O:45])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CN(C)C1C=CN=CC=1.O1CCCC1>[C:36]1([CH2:42][CH2:43][C:44]([N:8]([CH:9]2[CH2:10][CH2:11][CH:12]([C:15]3[CH:16]=[CH:17][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:24][CH:25]=3)[CH2:13][CH2:14]2)[C@H:7]2[CH2:6][C@H:5]3[CH2:26][C@H:3]([C:4]3([CH3:28])[CH3:27])[C@@H:2]2[CH3:1])=[O:45])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 64801Benzenepropanoyl chlorideHCID 67388866HCID 67388866, compound

Product 1

HCID 67389261HCID 67389261, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 45C (192 mg, 0.5 mmol), triethylamine (0.077 mL, 0.55 mmol) and 4-dimethylaminopyridine (6 mg, 0.05 mmol) in tetrahydrofuran (5 mL) was added 3-phenylpropanoyl chloride (0.082 mL, 0.55 mmol), and the reaction was stirred for 24 hours. The residue was chromatographed on silica gel using 20-50% ethyl acetate in hexanes to afford the title compound.

Workup

  1. customThe residue was chromatographed on silica gel using 20-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6de11c1906c24de7a313442cd186a732
Source dataset
uspto-grants-2012_05
Patent number
US08188077B2

Reaction notes

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