Sodium Bicarbonate → HCID 86635320, compound

HRID 656929Notes

Reaction equation

HRID 656929 reaction equation
[O:1]=[C:2]1[N:11]([CH2:12][CH:13]=O)[C:10]2[N:9]=[C:8]([C:15]#[N:16])[CH:7]=[CH:6][C:5]=2[CH:4]=[CH:3]1.[O:17]1[C:26]2[CH:25]=[C:24]([CH2:27][N:28]([CH:36]3[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]3)[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[N:23]=[CH:22][C:21]=2[O:20][CH2:19][CH2:18]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.CO>[C:15]([C:8]1[N:9]=[C:10]2[C:5]([CH:4]=[CH:3][C:2](=[O:1])[N:11]2[CH2:12][CH2:13][N:39]2[CH2:38][CH2:37][CH:36]([N:28]([CH2:27][C:24]3[N:23]=[CH:22][C:21]4[O:20][CH2:19][CH2:18][O:17][C:26]=4[CH:25]=3)[C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:34])[CH3:32])[CH2:41][CH2:40]2)=[CH:6][CH:7]=1)#[N:16]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 578154611,1-Dimethylethyl (2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)-4-piperidinylcarbamateHCID 86635319HCID 86635319, compound

Product 1

HCID 86635320HCID 86635320, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 7-oxo-8-(2-oxoethyl)-7,8-dihydro-1,8-naphthyridine-2-carbonitrile (329 mg, 1.545 mmol) and 1,1-dimethylethyl (2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)-4-piperidinylcarbamate (for a synthesis see WO2004/058144 Example 99(h)) (539 mg, 1.545 mmol) in chloroform (15 ml) and MeOH (1 ml) was stirred for 2 h before addition of NaBH(OAc)3 (982 mg, 4.635 mmol). The reaction was stirred for 0.5 h before addition of sat. aq NaHCO3 (50 ml). The reaction was then extracted with 20% MeOH in DCM (3×200 ml). The combined organic phases were dried, evaporated and the crude residue purified by chromatography on silica gel using a 0-20% MeOH/DCM gradient to provide the desired compound (620 mg, 73%).

Workup

  1. extractionThe reaction was then extracted with 20% MeOH in DCM (3×200 ml)
  2. customThe combined organic phases were dried
  3. customevaporated
  4. customthe crude residue purified by chromatography on silica gel using a 0-20% MeOH/DCM gradient

Sources & evidence

ORD record
ord-fbbb6f6286da4d21bdc515f8d25bd30e
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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