Trimethylsilyl isocyanate → HCID 86646714, compound

HRID 1809105Notes

Reaction equation

HRID 1809105 reaction equation
[N:1]1([C:11]([C:13]2[CH:17]=[C:16]([CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[S:15][CH:14]=2)=[O:12])[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.C[Si]([N:28]=[C:29]=[O:30])(C)C>C(Cl)Cl>[N:1]1([C:11]([C:13]2[CH:17]=[C:16]([CH:18]3[CH2:19][CH2:20][N:21]([C:29]([NH2:28])=[O:30])[CH2:22][CH2:23]3)[S:15][CH:14]=2)=[O:12])[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanate2×HCID 86646702cis-(Octahydro-quinolin-1-yl)-(5-piperidin-4-yl-thiophen-3-yl)-methanone

Product 1

HCID 86646714HCID 86646714, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of cis-(octahydro-quinolin-1-yl)-(5-piperidin-4-yl-thiophen-3-yl)-methanone (CC-033) (0.053 g, 0.16 mmol) in DCM (1 mL) was added trimethylsilylisocyanate (1.6 mmol). The mixture was stirred at room temperature overnight and then more trimethylsilylisocyanate (1.6 mmol) was added and the mixture stirred for a further 5 hours. The solution was diluted with DCM (10 mL) and washed with water. The resulting organic solution was dried and the solvent evaporated. The resulting oil was purified by HPLC, eluting with 10%-98% acetonitrile in water (0.1% formic acid). The fractions containing the desired product were concentrated under vacuum to give the title compound as a colourless oil (0.014 g). LCMS m/z 376.12 [M+H]+ RT=8.89 min (Analytical Method 2). 1H NMR (400 MHz, CHCl3-d): δ 7.25 (s, 1H), 6.9 (s, 1H), 4.7 (s, 2H), 4.6 (m, 1H), 4.1 (m, 2H), 3.8 (m, 1H), 3.2-2.7 (m, 4H), 2.1-1.05 (m, 17H).

Workup

  1. stirringthe mixture stirred for a further 5 hours
  2. washwashed with water
  3. customThe resulting organic solution was dried
  4. customthe solvent evaporated
  5. customThe resulting oil was purified by HPLC
  6. washeluting with 10%-98% acetonitrile in water (0.1% formic acid)
  7. additionThe fractions containing the desired product
  8. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-f6473bacbd994e19b09e5781ed4bcc76
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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