Trimethylsilyldiazomethane → HCID 86684745, compound

HRID 2401154Notes

Reaction equation

HRID 2401154 reaction equation
[Si](C=[N+]=[N-])(C)(C)[CH3:2].[OH:8][C@@H:9]1[CH2:13][O:12][C@@H:11]2[C@H:14]([O:17][C:18]3[N:19]([CH2:49][O:50][CH2:51][CH2:52][Si:53]([CH3:56])([CH3:55])[CH3:54])[C:20]4[C:21]([N:48]=3)=[N:22][C:23]([C:27]3[CH:32]=[CH:31][C:30]([C:33]5[N:38]=[CH:37][C:36]([N:39]6[CH:43]=[C:42]([CH2:44][C:45]([OH:47])=[O:46])[CH:41]=[N:40]6)=[CH:35][CH:34]=5)=[CH:29][CH:28]=3)=[C:24]([Cl:26])[CH:25]=4)[CH2:15][O:16][C@H:10]12>CO.C(Cl)Cl>[OH:8][C@@H:9]1[CH2:13][O:12][C@@H:11]2[C@H:14]([O:17][C:18]3[N:19]([CH2:49][O:50][CH2:51][CH2:52][Si:53]([CH3:55])([CH3:54])[CH3:56])[C:20]4[C:21]([N:48]=3)=[N:22][C:23]([C:27]3[CH:32]=[CH:31][C:30]([C:33]5[N:38]=[CH:37][C:36]([N:39]6[CH:43]=[C:42]([CH2:44][C:45]([O:47][CH3:2])=[O:46])[CH:41]=[N:40]6)=[CH:35][CH:34]=5)=[CH:29][CH:28]=3)=[C:24]([Cl:26])[CH:25]=4)[CH2:15][O:16][C@H:10]12

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 86684746HCID 86684746, compound

Product 1

HCID 86684745HCID 86684745, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

TMS-Diazomethane (2 M in hexanes, 0.15 mL, 0.300 mmol) was added to a stirred solution of 2-[1-[6-[4-[2-[[(3R,3aR,6R,6aR)-3-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl]oxy]-6-chloro-1-(2-trimethylsilylethoxymethyl)-imidazo[4,5-b]pyridin-5-yl]phenyl]-3-pyridyl]pyrazol-4-yl]acetic acid (27.3 mg, 0.039 mmol) in MeOH (0.5 mL) and DCM (0.5 mL). The reaction mixture was stirred at room temperature. After 3.5 hours, the reaction mixture was evaporated under reduced pressure to give the desired compound as a yellow residue. This material was used in the next step without further purification. LC-MS: calculated for C35H39ClN6O7Si 718.23 observed m/e: 719.31 (M+H)+ (Rt 1.26/2 min).

Workup

  1. customthe reaction mixture was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9f9bcfed3a9145cb9f962f58e8e2de92
Source dataset
uspto-grants-2014_08
Patent number
US08796258B2

Reaction notes

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