Dichloromethane → HCID 90067529, compound

HRID 929225Notes

Reaction equation

HRID 929225 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[N:22](COCC[Si](C)(C)C)[C:21]([O:31][C@H:32]3[C@H:36]4[O:37][CH2:38][CH:39]([CH2:40][C:41]([NH2:43])=[O:42])[C@H:35]4[O:34][CH2:33]3)=[N:20][C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.C(Cl)Cl>C(O)(C(F)(F)F)=O.CO>[Cl:1][C:2]1[CH:3]=[C:4]2[NH:22][C:21]([O:31][C@H:32]3[C@H:36]4[O:37][CH2:38][CH:39]([CH2:40][C:41]([NH2:43])=[O:42])[C@H:35]4[O:34][CH2:33]3)=[N:20][C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 1317350992-[(3aR,6R,6aS)-6-[6-chloro-5-(4-phenylphenyl)-1-(2-trimethylsilylethoxy-methyl)-imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl]acetamide

Product 1

HCID 90067529HCID 90067529, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

2-[(3aR,6R,6aS)-6-[6-chloro-5-(4-phenylphenyl)-1-(2-trimethylsilylethoxymethyl)-imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl]acetamide was dissolved in TFA (0.5 mL) and DCM (0.5 mL) and stirred at room temperature for 2 hours. The reaction mixture was evaporated to give an oil. The oil was dissolved in methanol (0.5 mL) and purified by preparative HPLC reverse phase (C-18), using a 30×150 mm Sunfire™ column and eluting with a 20%-80% acetonitrile/water+0.05% TFA gradient. The desired fractions were lyophilized to give the title compound as a solid. Major isomer LC-MS: calculated for C26H23ClN4O4 490.14 observed m/e: 491.23 (M+H)+ (Rt 0.53/2 min); 1H NMR δ (ppm) (CD3OD): 7.94 (s, 1H), 7.76 (ABq, 4H), 7.71 (d, 2H), 7.48 (dd, 2H), 7.38 (dd, 1H), 5.58 (qt, 1H), 5.00 (t, 1H), 4.56 (t, 1H), 4.12 (dd, 1H), 4.02 (m, 2H), 3.54 (dd, 1H), 2.64 (dd, 1H), 2.58 (m, 1H) and 2.38 (dd, 1H).

Workup

  1. customThe reaction mixture was evaporated
  2. customto give an oil
  3. custompurified by preparative HPLC reverse phase (C-18)
  4. washeluting with a 20%-80% acetonitrile/water+0.05% TFA gradient

Sources & evidence

ORD record
ord-a13389f8a22b443985004709559531c8
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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