Tetrabutylammonium Fluoride → HCID 131728741, compound

HRID 601527Notes

Reaction equation

HRID 601527 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[C:11](=[O:41])[N:12]([C:17]4[CH:22]=[CH:21][C:20]([N:23]5[CH2:27][CH2:26][C@@H:25]([O:28][Si](C(C)C)(C(C)C)C(C)C)[CH2:24]5)=[C:19]([O:39][CH3:40])[CH:18]=4)[CH2:13][CH2:14][C:15]=3[N:16]=2)=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]3[C:11](=[O:41])[N:12]([C:17]4[CH:22]=[CH:21][C:20]([N:23]5[CH2:27][CH2:26][C@@H:25]([OH:28])[CH2:24]5)=[C:19]([O:39][CH3:40])[CH:18]=4)[CH2:13][CH2:14][C:15]=3[N:16]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57870237HCID 57870237, compound

Product 1

HCID 131728741HCID 131728741, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve (R)-2-(4-chloro-phenyl)-5-[3-methoxy-4-(3-triisopropylsilanyloxy-pyrrolidin-1-yl)-phenyl]-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one (370 mg, 0.610 mmol) in dry THF (2 mL). Add TBAF (1.0M in THF, 610 μl, 0.610 mmol) and stir 2 h. Absorb the reaction mixture on silica gel and remove organic solvent via reduce pressure. Purify by silica gel chromatography using 0-100% EtOAc in hexanes to give the title compound. Dissolve the compound in a minimal amount of CH2Cl2 and add HCl/Et2O solution to give precipitated product. Remove the organic solvent via reduced pressure and triturate with MeOH to give the desired product as white solid HCl salt (144 mg, 48%). MS (ES+) 456.0 (M+1)+. 1H NMR (CD3OD): δ 8.01 (d, J=8.8 Hz, 2H), 7.71 (br d, J=8.8 Hz, 1H), 7.51 (d, J=8.4 Hz, 2H), 7.35 (br s, 1H), 7.16 (br d, J=8.8 Hz, 1H), 4.73-4.67 (m, 1H), 4.19 (br t, J=6.6 Hz, 2H), 4.02 (br s, 3H), 3.97-3.85 (m, 3H), 3.66 (br d, J=11.0 Hz, 1H), 3.31 (t, J=7.0 Hz, 2H), 2.49-2.36 (m, 1H), 2.26-2.17 (m, 1H).

Workup

  1. customAbsorb the reaction mixture on silica gel
  2. customremove organic solvent
  3. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-93906293dbff42d0b426ccb15c126e62
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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