Ethanol → HCID 90067288, compound

HRID 929148Notes

Reaction equation

HRID 929148 reaction equation
C(O)(C(F)(F)F)=O.[Si]([O:15][C@H:16]1[C@H:20]2[O:21][CH2:22][C@@H:23]([O:24][C:25]3[N:26]([CH2:56][CH:57]=[CH2:58])[C:27]4[C:28]([N:55]=3)=[N:29][C:30]([C:34]3[CH:39]=[CH:38][C:37]([N:40]5[CH:44]=[C:43]6[CH2:45][N:46](C(OC(C)(C)C)=O)[CH2:47][C:42]6=[N:41]5)=[CH:36][CH:35]=3)=[C:31]([Cl:33])[CH:32]=4)[C@H:19]2[O:18][CH2:17]1)(C(C)(C)C)(C)C.[NH4+].[OH-].CO.C(O)C>C(Cl)Cl.C1C=CC=CC=1>[CH2:56]([N:26]1[C:27]2[C:28](=[N:29][C:30]([C:34]3[CH:35]=[CH:36][C:37]([N:40]4[CH:44]=[C:43]5[CH2:45][NH:46][CH2:47][C:42]5=[N:41]4)=[CH:38][CH:39]=3)=[C:31]([Cl:33])[CH:32]=2)[N:55]=[C:25]1[O:24][C@H:23]1[C@H:19]2[O:18][CH2:17][C@@H:16]([OH:15])[C@H:20]2[O:21][CH2:22]1)[CH:57]=[CH2:58]

Participants

7

Reactant 4

HCID 702EthanolHCID 6422Trifluoroacetic acidHCID 21894508Ammonium hydroxide methanol2×HCID 131735087HCID 131735087, compound

Product 1

HCID 90067288HCID 90067288, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent3×

Procedure

TFA (3.2 ml, 41.5 mmol) was added to a stirred solution of tert-butyl 2-[4-[2-[[(3R,3aR,6R,6aS)-6-[tert-butyl(dimethyl)silyl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl]oxy]-1-allyl-6-chloro-imidazo[4,5-b]pyridin-5-yl]phenyl]-4,6-dihydropyrrolo[3,4-c]pyrazole-5-carboxylate (477.4 mg, 0.649 mmol) in DCM (3.2 ml). The reaction mixture was a pale yellow solution that was stirred at room temperature for 3 days. The reaction mixture was evaporated under reduced pressure to give a light yellow oil. Flash chromatography of the oil utilizing a 40 g silica RediSep Rf® column and employing a 0-10% (10% NH4OH/MeOH)/DCM gradient followed by 10% (10% NH4OH/MeOH)/DCM afforded the title compound as an off-white solid following lyophilization from ethanol and benzene. LC-MS: calculated for C26H25ClN6O4 520.16 observed m/e: 521.15 (M+H)+ (Rt 1.00/2 min)

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customto give a light yellow oil

Sources & evidence

ORD record
ord-d3c9374a2fb94a74b13f95d1d633c750
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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