Ammonia → HCID 57687045, compound

HRID 908484Notes

Reaction equation

HRID 908484 reaction equation
[CH2:1]=O.[NH2:3][C:4]1[C:9]([C:10]2[O:11][C:12]3[C:18]([CH2:19][OH:20])=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:8][C:7]([C:21]2[CH:22]=[N:23][N:24]([CH:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[CH:25]=2)=[CH:6][N:5]=1.[Na].N>ClCCl.CO>[NH2:3][C:4]1[C:9]([C:10]2[O:11][C:12]3[C:18]([CH2:19][OH:20])=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:8][C:7]([C:21]2[CH:22]=[N:23][N:24]([CH:26]3[CH2:31][CH2:30][N:29]([CH3:1])[CH2:28][CH2:27]3)[CH:25]=2)=[CH:6][N:5]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 712FormaldehydeHCID 5360545SodiumHCID 67388416HCID 67388416, compound

Product 1

HCID 57687045HCID 57687045, 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 [2-[2-amino-5-[1-(4-piperidyl)pyrazol-4-yl]-3-pyridyl]-1,3-benzoxazol-7-yl]methanol (46 mg) dissolved in dichloromethane (2 ml) and methanol (2 ml) over a period of 5 minutes. The resulting solution was stirred at 0° C. for 10 minutes. Sodium triacetoxyhydroborate (30.0 mg) was added at 0° C. to the mixture and stirred at 0° C. for 1 hour. A solution 7N of 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 4 to 8% methanolic ammonia (7 N) in dichloromethane. The solvent was evaporated to dryness and the product was recrystallized from acetonitrile to afford [2-[2-amino-5-[1-(1-methyl-4-piperidyl)pyrazol-4-yl]-3-pyridyl]-1,3-benzoxazol-7-yl]methanol (37.0 mg) as a solid. NMR Spectrum: (CDCl3) 2.05-2.29 (m, 6H), 2.36 (s, 3H), 2.98-3.08 (m, 2H), 4.12-4.23 (m, 1H), 5.09 (s, 2H), 6.88 (bs, 2H), 7.37 (dd, 1H), 7.43 (d, 1H), 7.66 (d, 1H), 7.67 (s, 1H), 7.74 (s, 1H), 8.30 (d, 1H), 8.32 (d, 1H); Mass spectrum: M+H+ 405;

Workup

  1. stirringstirred at 0° C. for 1 hour
  2. customThe crude product was purified by flash chromatography on silica gel eluting with 4 to 8% methanolic ammonia (7 N) in dichloromethane
  3. customThe solvent was evaporated to dryness
  4. customthe product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-33ff97cca0b042f495215cdf7dc28423
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

Loading…