Tetrabutylammonium Fluoride → HCID 58944604, compound

HRID 222205Notes

Reaction equation

HRID 222205 reaction equation
[Si]([O:8][C@H:9]1[CH2:13][C@H:12]([N:14]2[C:18]3[N:19]=[CH:20][N:21]=[C:22]([NH:23][C@@H:24]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[CH2:26][CH2:25]4)[C:17]=3[CH:16]=[CH:15]2)[CH2:11][C@H:10]1[CH2:33][CH2:34][S:35]([NH2:38])(=[O:37])=[O:36])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C@@H:24]1([NH:23][C:22]2[C:17]3[CH:16]=[CH:15][N:14]([C@@H:12]4[CH2:11][C@@H:10]([CH2:33][CH2:34][S:35]([NH2:38])(=[O:37])=[O:36])[C@@H:9]([OH:8])[CH2:13]4)[C:18]=3[N:19]=[CH:20][N:21]=2)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58944687HCID 58944687, compound

Product 1

HCID 58944604HCID 58944604, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-((1S,2S,4R)-2-[tert-butyl(dimethyl)silyl]oxy-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)ethanesulfonamide (32 mg, 0.000057 mol) was dissolved in tetrahydrofuran (1.0 mL, 0.012 mol) and a 1.00 M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (0.100 mL) was added. The mixture was stirred at room temperature for 1 hour. The reaction mixture was quenched with a little water and then concentrated. Purification of the residue by silica gel chromatography, eluting with 0 to 100% of (9:1 EtOAc:EtOH) in DCM, afforded the desired product, (9 mg, 40%). 1H-NMR (400 MHz, MeOD, δ): 8.16 (s, 1H), 7.19 (m, 5H), 6.62 (d, J=3.6 Hz, 1H), 5.85 (t, J=7.7 Hz, 1H), 5.43 (dddd, J=4.2 Hz, 8.4 Hz, 8.4 Hz, 8.4 Hz, 1H), 4.35 (t, J=3.7 Hz, 1H), 3.13 (m, 3H), 2.91 (m, 1H), 2.63 (m, 1H), 2.49 (m, 1H), 2.35 (ddd, J=1.2 Hz, 8.1 Hz, 13.8 Hz, 1H), 2.05 (m, 6H). LC/MS: Rt=1.07 min, ES+ 442 (AA standard).

Workup

  1. customThe reaction mixture was quenched with a little water
  2. concentrationconcentrated
  3. customPurification of the residue by silica gel chromatography
  4. washeluting with 0 to 100% of (9:1 EtOAc:EtOH) in DCM

Sources & evidence

ORD record
ord-6b9bcc5538254ba28bad3cbc18de3d5a
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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