Diphosgene → HCID 178455382, compound

HRID 715602Notes

Reaction equation

HRID 715602 reaction equation
[Si:1]([O:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C@@H:16]([O:17][C:18]3[N:40]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])[C:21]4=[N:22][C:23]([C:27]5[CH:32]=[CH:31][C:30]([C@H:33]6[CH2:38][CH2:37][C@H:36]([NH2:39])[CH2:35][CH2:34]6)=[CH:29][CH:28]=5)=[C:24]([Cl:26])[CH:25]=[C:20]4[N:19]=3)[C@H:12]2[O:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[O:49]=[C:50](Cl)[O:51][C:52](Cl)(Cl)Cl.[O:57]1[CH2:62][CH2:61]C(O)[CH2:59][CH2:58]1>C1(C)C=CC=CC=1>[Si:1]([O:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C@@H:16]([O:17][C:18]3[N:40]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])[C:21]4=[N:22][C:23]([C:27]5[CH:32]=[CH:31][C:30]([C@H:33]6[CH2:38][CH2:37][C@H:36]([NH:39][C:50](=[O:49])[O:51][CH:52]7[CH2:61][CH2:62][O:57][CH2:58][CH2:59]7)[CH2:35][CH2:34]6)=[CH:29][CH:28]=5)=[C:24]([Cl:26])[CH:25]=[C:20]4[N:19]=3)[C@H:12]2[O:11][CH2:10]1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10426DiphosgeneHCID 74956Tetrahydro-4H-pyran-4-olHCID 178455378HCID 178455378, compound

Product 1

HCID 178455382HCID 178455382, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

(trans)-4-(4-(2-((3R,3aR,6R,6aS)-6-(tert-Butyldimethylsilyloxy)hexahydrofuro[3,2-b]furan-3-yloxy)-6-chloro-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridin-5-yl)phenyl)cyclohexanamine (20 mg) is dissolved in toluene (2 mL), treated dropwise with a solution of diphosgene (3.4 μL) in toluene (1 mL) and stirred for 12 hours at 60° C. Tetrahydro-2H-pyran-4-ol (2.7 μL) is added and the mixture is heated for 12 hours at 60° C. The mixture is partitioned between ethylacetate and saturated aqueous NH4Cl solution. The organic phase is washed with brine, dried (MgSO4) and concentrated to give the title compound. LC (method 5): tR=1.22 min.

Workup

  1. temperaturethe mixture is heated for 12 hours at 60° C
  2. customThe mixture is partitioned between ethylacetate and saturated aqueous NH4Cl solution
  3. washThe organic phase is washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e688e89b9117400082d53ca895429417
Source dataset
uspto-grants-2015_11
Patent number
US09187477B2

Reaction notes

Loading…