Water → HCID 178455378, compound

HRID 715598Notes

Reaction equation

HRID 715598 reaction equation
[N:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[N:21]=[C:20]4[N:22]([CH2:42][O:43][CH2:44][CH2:45][Si:46]([CH3:49])([CH3:48])[CH3:47])[C:23]([O:25][C@@H:26]5[CH2:30][O:29][C@@H:28]6[C@H:31]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[CH2:32][O:33][C@H:27]56)=[N:24][C:19]4=[CH:18][C:17]=3[Cl:50])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[Si:35]([O:34][C@H:31]1[C@H:28]2[O:29][CH2:30][C@@H:26]([O:25][C:23]3[N:22]([CH2:42][O:43][CH2:44][CH2:45][Si:46]([CH3:49])([CH3:48])[CH3:47])[C:20]4=[N:21][C:16]([C:13]5[CH:14]=[CH:15][C:10]([C@H:7]6[CH2:8][CH2:9][C@H:4]([NH2:1])[CH2:5][CH2:6]6)=[CH:11][CH:12]=5)=[C:17]([Cl:50])[CH:18]=[C:19]4[N:24]=3)[C@H:27]2[O:33][CH2:32]1)([C:38]([CH3:40])([CH3:41])[CH3:39])([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 178455384HCID 178455384, compound

Product 1

HCID 178455378HCID 178455378, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

5-(4-((trans)-4-Azidocyclohexyl)phenyl)-2-((3R,3aR,6R,6aS)-6-(tert-butyldimethyl-silyloxy)hexahydrofuro[3,2-b]furan-3-yloxy)-6-chloro-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridine (130 mg) is dissolved in tetrahydrofurane (1 mL), treated with triphenylphosphine (57 mg) and stirred for 24 hours at 40° C. Then water (220 μL) is added and the mixture is stirred for 12 hours at 80° C. The mixture is partitioned between ethylacetate and saturated aqueous NH4Cl solution. The organic phase is dried (MgSO4) and concentrated. The residue is purified by HPLC on reversed phase to give the product, which is partitioned between 1 M aqueous NaOH solution and ethylacetate. The organic phase is washed with brine and dried (MgSO4). The residue is concentrated to give the title compound. LC (method 1): tR=1.24 min; Mass spectrum (ESI+): m/z=715 [M+H]+.

Workup

  1. stirringthe mixture is stirred for 12 hours at 80° C
  2. customThe mixture is partitioned between ethylacetate and saturated aqueous NH4Cl solution
  3. dry with materialThe organic phase is dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue is purified by HPLC on reversed phase
  6. customto give the product, which
  7. customis partitioned between 1 M aqueous NaOH solution and ethylacetate
  8. washThe organic phase is washed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationThe residue is concentrated

Sources & evidence

ORD record
ord-e3c0b06099f34495a827261220dd61f2
Source dataset
uspto-grants-2015_11
Patent number
US09187477B2

Reaction notes

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