Ammonia → HCID 42599360, compound

HRID 908373Notes

Reaction equation

HRID 908373 reaction equation
[CH2:1]=O.[F:3][C:4]1[C:9]2[N:10]=[C:11]([C:13]3[C:14]([NH2:30])=[N:15][CH:16]=[C:17]([C:19]4[CH:20]=[N:21][N:22]([CH:24]5[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]5)[CH:23]=4)[CH:18]=3)[O:12][C:8]=2[CH:7]=[CH:6][CH:5]=1.[Na].N>ClCCl.CO>[F:3][C:4]1[C:9]2[N:10]=[C:11]([C:13]3[C:14]([NH2:30])=[N:15][CH:16]=[C:17]([C:19]4[CH:20]=[N:21][N:22]([CH:24]5[CH2:25][CH2:26][N:27]([CH3:1])[CH2:28][CH2:29]5)[CH:23]=4)[CH:18]=3)[O:12][C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 712FormaldehydeHCID 5360545SodiumHCID 67389182HCID 67389182, compound

Product 1

HCID 42599360HCID 42599360, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

37% aqueous formaldehyde (0.015 ml) at 0° C., was added to a stirred solution of 3-(4-fluoro-1,3-benzoxazol-2-yl)-5-[1-(4-piperidyl)pyrazol-4-yl]pyridin-2-amine dissolved in dichloromethane (6 ml) and methanol (6 ml) over a period of 5 minutes. The resulting mixture was stirred at 0° C. for 10 minutes. Sodium triacetoxyhydroborate (233 mg) was added at 0° C. to the mixture and stirred at 0° C. for 1 hour. A solution of 7N ammonia in methanol (20 ml) was added to the mixture and adsorbed on silica gel. The crude product was purified by flash chromatography on silica gel eluting with 2 to 6% methanolic ammonia (7 N) in dichloromethane. The solvent was evaporated to dryness and tritured in hot acetonitrile, filtered and dried under reduce pressure to afford 3-(4-fluoro-1,3-benzoxazol-2-yl)-5-[1-(1-methyl-4-piperidyl)pyrazol-4-yl]pyridin-2-amine (268 mg) as a solid.

Workup

  1. stirringstirred at 0° C. for 1 hour
  2. customThe crude product was purified by flash chromatography on silica gel eluting with 2 to 6% methanolic ammonia (7 N) in dichloromethane
  3. customThe solvent was evaporated to dryness and tritured in hot acetonitrile
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-b341063889e3443abefe4d68b1dea6ce
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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