Hydrochloric Acid → HCID 178514807, compound

HRID 1747660Notes

Reaction equation

HRID 1747660 reaction equation
[Si]([O:8][C@H:9]1[CH2:13][C@H:12]([O:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]3[NH:21][C:22]([C:24]4[C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[CH:27]=[CH:26][CH:25]=4)=[N:23][C:16]=23)[CH2:11][C@H:10]1[CH2:34][OH:35])(C(C)(C)C)(C)C.Cl[S:37]([NH2:40])(=[O:39])=[O:38].Cl.C([O-])([O-])=O.[Na+].[Na+]>CC(N(C)C)=O.O>[S:37](=[O:39])(=[O:38])([O:35][CH2:34][C@@H:10]1[CH2:11][C@@H:12]([O:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]3[NH:21][C:22]([C:24]4[C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[CH:27]=[CH:26][CH:25]=4)=[N:23][C:16]=23)[CH2:13][C@@H:9]1[OH:8])[NH2:40]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 24499Chlorosulfamic acidHCID 178455375HCID 178455375, compound

Product 1

HCID 178514807HCID 178514807, compoundYield 25.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of ((1S,2S,4R)-2-{[tert-butyl(dimethyl)silyl]oxy}-4-{[2-(1-naphthyl)-3H-imidazo[4,5-b]pyridin-7-yl]oxy}cyclopentyl)methanol (0.0624 g, 0.000127 mol) in DMA (2.00 mL) was added chlorosulfonamide (0.0736 g, 0.000637 mol) and the mixture was stirred for 10 min. To this was added 12 M of hydrochloric acid in water (2.00 mL) dropwise at 0° C. and the mixture was stirred for 10 min. The mixture was added dropwise to 50 mL of a 2N Na2CO3 solution, and was extracted by CH2Cl2 (3×30 ml). The combined organic layers were concentrated and the residue was purified by flash chromatography (0 to 10% MeOH/EtOAc) to provide the title compound (14.5 mg, 25%) as a white solid. 1H NMR (CD3OD, 400 MHz) δ: 8.49 (m, 1H,), 8.28 (m, 1H), 8.06 (d, 1H, J=8.3 Hz), 7.97 (m, 1H), 7.87 (dd, 1H, J=7.0 Hz, J=1.0 Hz) 7.63-7.54 (m, 3H), 6.89 (d, 1H, J=5.8 Hz) 5.40 (bs, 1H), 4.45 (dt, 1H, J=4.9 Hz, J=1.9 Hz), 4.35 (dd, 1H, J=7.2 Hz, J=2.5 Hz), 4.19 (dd, 1H, J=7.2 Hz, J=2.5 Hz), 2.62 (m, 1H), 2.44-2.39 (m, 1H), 2.31-2.25 (m, 1H), 2.18-2.14 (m, 2H). LC/MS: Rt=1.55 min, ES+ 455 (AA standard).

Workup

  1. stirringthe mixture was stirred for 10 min
  2. extractionwas extracted by CH2Cl2 (3×30 ml)
  3. concentrationThe combined organic layers were concentrated
  4. customthe residue was purified by flash chromatography (0 to 10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-72a17573d082420d9606c625b287d63e
Source dataset
uspto-grants-2015_10
Patent number
US09150525B2

Reaction notes

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