Chlorotrimethylsilane → HCID 178427949, compound

HRID 2218412Notes

Reaction equation

HRID 2218412 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:18][C:11]3=[N:12][CH:13]=[C:14]([Cl:17])[C:15]([CH3:16])=[C:10]3[N:9]=2)=[CH:4][C:3]=1[OH:19].[CH:20]([C@H:22]1[CH2:26][CH2:25][CH2:24][N:23]1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=O.C[Si](Cl)(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CN1C(=O)CCC1.C(O)(=O)C>[Cl:17][C:14]1[C:15]([CH3:16])=[C:10]2[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][CH2:20][C@H:22]4[CH2:26][CH2:25][CH2:24][N:23]4[C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])=[C:3]([OH:19])[CH:4]=3)[NH:18][C:11]2=[N:12][CH:13]=1

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 5049666Sodium triacetoxyborohydrideHCID 7009153N-(tert-Butoxycarbonyl)-D-prolinalHCID 178427951HCID 178427951, compound

Product 1

HCID 178427949HCID 178427949, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2-Amino-5-(6-chloro-7-methyl-3H-imidazo[4,5-b]pyridin-2-yl)phenol (Example 249) (0.050 g, 0.18 mmol) and tert-butyl (2R)-2-formylpyrrolidine-1-carboxylate (0.036 g, 0.18 mmol) were dissolved in NMP (1.0 ml) and acetic acid (0.10 ml). TMSCl (0.046 ml, 0.36 mmol) and NaBH(OAc)3 (0.072 g, 0.36 mmol) were added and the mixture stirred overnight. The crude mixture was purified by HPLC-C18 giving the title compound (0.017 g, 21%).

Workup

  1. customThe crude mixture was purified by HPLC-C18 giving the title compound (0.017 g, 21%)

Sources & evidence

ORD record
ord-6c585ee1875d46b3a62cb9a4c77e99fb
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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