Ammonium Chloride → HCID 44199824, compound

HRID 2061178Notes

Reaction equation

HRID 2061178 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([CH3:12])[CH:10]=2)[CH:5]=[C:4]([C:13]2[CH:14]=[C:15]([NH:20][C:21]3[N:25]=[C:24]([C:26]4([C:29]([O-])=[O:30])[CH2:28][CH2:27]4)[O:23][N:22]=3)[CH:16]=[CH:17][C:18]=2[CH3:19])[C:3]1=[O:32].[BH4-].[Na+].[Cl-].[NH4+]>CO>[OH:30][CH2:29][C:26]1([C:24]2[O:23][N:22]=[C:21]([NH:20][C:15]3[CH:16]=[CH:17][C:18]([CH3:19])=[C:13]([C:4]4[C:3](=[O:32])[N:2]([CH3:1])[C:11]5[C:6]([CH:5]=4)=[CH:7][N:8]=[C:9]([CH3:12])[CH:10]=5)[CH:14]=3)[N:25]=2)[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 86656154HCID 86656154, compound

Product 1

HCID 44199824HCID 44199824, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(3-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenylamino)-1,2,4-oxadiazol-5-yl)cyclopropanecarboxylate 23 (100 mg, 0.22 mmol) in MeOH (10 mL), three batches of NaBH4 (66.5 mg, 1.76 mmol) were added during a period of 30 min. After the reaction was determined to be completed by LC/MS, ammonium chloride solution was added to quench the reaction. The resulting mixture was extracted with DCM (50 mL). The organic layer was dried over Na2SO4, filtered and evaporated to yield a reside which was purified by preparative HPLC to yield 3-(5-(5-(1-(hydroxymethyl)cyclopropyl)-1,2,4-oxadiazol-3-ylamino)-2-methylphenyl)-1,7-di methyl-1,6-naphthyridin-2(1H)-one (A69). 1H NMR (400 MHz, d6-DMSO) δ 9.07 (s, 1H), 8.03 (s, 1H), 7.91 (s, 1H), 7.41 (d, J=2.4 Hz, 1H), 7.33 (dd, J=2.4, 8.4 Hz, 1H), 7.23 (d, J=8.4 Hz, 1H), 3.87 (s, 2H), 3.83 (s, 3H), 2.86 (s, 3H), 2.16 (s, 3H), 1.35 (m, 2H), 1.21 (m, 2H). MS m/z 418.2 (M+1).

Workup

  1. additionwas added
  2. customto quench
  3. customthe reaction
  4. extractionThe resulting mixture was extracted with DCM (50 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customto yield a reside which
  9. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-6d8e5a2ff02d41358126a0ca5e0467ea
Source dataset
uspto-grants-2012_10
Patent number
US08278452B2

Reaction notes

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