Trimethylsilyl isocyanate → HCID 57595489, compound

HRID 1786033Notes

Reaction equation

HRID 1786033 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:35]=[CH:34][C:9]([C:10]([N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C@H:15]([N:22]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[C:23](=[O:25])[CH3:24])[CH2:14][C@@H:13]2[CH3:33])=[O:11])=[CH:8][CH:7]=1.C[Si]([N:40]=[C:41]=[O:42])(C)C>C(Cl)Cl>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([N:22]([C@H:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:12]([C:10](=[O:11])[C:9]3[CH:8]=[CH:7][C:6]([O:5][CH2:4][CH2:3][CH2:2][NH:1][C:41]([NH2:40])=[O:42])=[CH:35][CH:34]=3)[C@@H:13]([CH3:33])[CH2:14]2)[C:23](=[O:25])[CH3:24])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 58859953HCID 58859953, compound

Product 1

HCID 57595489HCID 57595489, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4R)-N-{1-[4-(3-Amino-propoxy)-benzoyl]-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl}-N-(4-chloro-phenyl)-acetamide (50 mg, 0.10 mmol) in DCM (1 mL) was added trimethylsilyl isocyanate (23 mg, 0.20 mmol). The reaction mixture was stirred at room temperature for 18 hours. The reaction was quenched by adding 0.2 mL of water and concentrated under reduced pressure. The crude residue was purified by preparatory HPLC to afford the product (9 mg, 17%).

Workup

  1. customThe reaction was quenched
  2. additionby adding 0.2 mL of water
  3. concentrationconcentrated under reduced pressure
  4. customThe crude residue was purified by preparatory HPLC

Sources & evidence

ORD record
ord-ff72a5a95c5149c4a3fe7f172e5afa93
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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