Trimethylsilyl isocyanate → HCID 46239391, compound

HRID 2066563Notes

Reaction equation

HRID 2066563 reaction equation
[CH2:1]1[C:4]2([CH2:9][CH2:8][NH:7][CH2:6][CH2:5]2)[CH2:3][N:2]1[CH2:10][C:11]1[S:19][C:18]2[C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[N:16][C:15]([C:26]3[C:34]([F:35])=[CH:33][CH:32]=[C:31]4[C:27]=3[CH:28]=[CH:29][NH:30]4)=[N:14][C:13]=2[CH:12]=1.C[Si]([N:40]=[C:41]=[O:42])(C)C>C(Cl)Cl>[F:35][C:34]1[C:26]([C:15]2[N:16]=[C:17]([N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)[C:18]3[S:19][C:11]([CH2:10][N:2]4[CH2:3][C:4]5([CH2:9][CH2:8][N:7]([C:41]([NH2:40])=[O:42])[CH2:6][CH2:5]5)[CH2:1]4)=[CH:12][C:13]=3[N:14]=2)=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][CH:29]=[CH:28]2

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 46239898HCID 46239898, compound

Product 1

HCID 46239391HCID 46239391, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(2,7-diaza-spiro[3.5]non-2-ylmethyl)-2-(5-fluoro-1H-indol-4-yl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (125 mg, 0.254 mmol) in anhydrous DCM (10 mL) was added trimethylsilyl isocyanate (35 μL, 0.254 mmol). The reaction mixture was stirred at RT for 1 h, then partitioned between DCM and a saturated aqueous solution of NaHCO3. The organic layer was separated and washed with brine, then dried (Na2SO4) and concentrated in vacuo. The resultant residue was purified by preparative HPLC to give the title compound as a white solid (41 mg, 30%).

Workup

  1. custompartitioned between DCM
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-2b3579804bd347d78ed7797579ee7f1d
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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