Water → HCID 89473219, compound

HRID 931617Notes

Reaction equation

HRID 931617 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]2[C@@:17]3([CH2:22][CH2:21][O:20][C:19]([NH2:23])=[N:18]3)[C:16]3[C:11](=[N:12][CH:13]=[C:14]([Br:24])[CH:15]=3)[O:10][C:7]2=[CH:8][CH:9]=1)=[N+]=[N-].[B-].[Na+].[BH4-].[Na+].O>CO.CCOC(C)=O>[Br:24][C:14]1[CH:15]=[C:16]2[C@:17]3([CH2:22][CH2:21][O:20][C:19]([NH2:23])=[N:18]3)[C:6]3[C:7](=[CH:8][CH:9]=[C:4]([NH2:1])[CH:5]=3)[O:10][C:11]2=[N:12][CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 4311764Sodium borohydride2×HCID 22959485VertellusHCID 117600802HCID 117600802, compound

Product 1

HCID 89473219HCID 89473219, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

(S)-7-azido-3-bromo-5′,6′-dihydrospiro[chromeno[2,3-b]pyridine-5,4′-[1,3]oxazin]-2′-amine (200 mg, 0.517 mmol) was dissolved in MeOH (2 mL) and sodium borohydrate (195 mg, 5.17 mmol) was added at rt. After 1 h, additional MeOH (2 mL) and 10 equiv of NaBH4 were added at rt. The reaction mixture was allowed to stir overnight. Additional MeOH (2 mL) and 10 equiv of NaBH4 were added and the reaction was allowed to stir for 1 h. Water was added, followed by EtOAc. The organic phase was separated, dried over MgSO4. The solvent was removed under reduced pressure to give (S)-3-bromo-5′,6′-dihydrospiro[chromeno[2,3-b]pyridine-5,4′-[1,3]oxazine]-2′,7-diamine as a light-yellow solid. The compound was used in the next step without further purification. MS m/z=362.8 [M+H]+. Calculated for C15H13BrN4O2: 361.19.

Workup

  1. stirringto stir for 1 h
  2. customThe organic phase was separated
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a4104730fab349c3a73066cab604c673
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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