Acetic Acid → HCID 86721020, compound

HRID 524963Notes

Reaction equation

HRID 524963 reaction equation
[NH2:1][C:2]1[C:11]([C:12]([NH:14][C:15]2[CH:24]=[N:23][CH:22]=[C:21]3[C:16]=2[CH2:17][CH2:18][N:19]([C:25](OC(C)(C)C)=O)[CH2:20]3)=[O:13])=[C:5]2[N:6]=[CH:7][C:8]([F:10])=[CH:9][N:4]2[N:3]=1.C(O)(=O)C.C=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO>[NH2:1][C:2]1[C:11]([C:12]([NH:14][C:15]2[C:16]3[CH2:17][CH2:18][N:19]([CH3:25])[CH2:20][C:21]=3[CH:22]=[N:23][CH:24]=2)=[O:13])=[C:5]2[N:6]=[CH:7][C:8]([F:10])=[CH:9][N:4]2[N:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86721021HCID 86721021, compound

Product 1

HCID 86721020HCID 86721020, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-butyl 5-(2-amino-6-fluoropyrazolo[1,5-a]pyrimidine-3-carboxamido)-3,4-dihydro-2,7-naphthyridine-2(1H)-carboxylate was dissolved in MeOH (8 mL). Acetic acid (91.88 mg, 87.01 μL, 1.530 mmol), formaldehyde (37% solution in water, 99.33 mg, 91.13 μL, 1.224 mmol) and NaBH(OAc)3 (324.3 mg, 1.530 mmol) was sequentially added and the mixture was stirred for 1 hour at RT. The reaction mixture was partitioned between an aqueous saturated solution of NaHCO3 and DCM. The insoluble was filtered off and the combined organic extract was dried and concentrated in vacuo. The insoluble and the residue were combined and purified by fractionlynx to yield 2-amino-6-fluoro-N-(7-methyl-5,6,7,8-tetrahydro-2,7-naphthyridin-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide. MS (ES+) 342.2.

Workup

  1. customThe reaction mixture was partitioned between an aqueous saturated solution of NaHCO3 and DCM
  2. filtrationThe insoluble was filtered off
  3. extractionthe combined organic extract
  4. customwas dried
  5. concentrationconcentrated in vacuo
  6. custompurified by fractionlynx

Sources & evidence

ORD record
ord-30adf4553653474f934547be84a4171d
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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