Ammonia → HCID 57687069, compound

HRID 908382Notes

Reaction equation

HRID 908382 reaction equation
C=O.[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[C:12]1[C:13]([NH2:29])=[N:14][CH:15]=[C:16]([C:18]2[CH:19]=[N:20][N:21]([CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[CH:22]=2)[N:17]=1.[C:30](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].N>CO.C(Cl)Cl>[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[C:12]1[C:13]([NH2:29])=[N:14][CH:15]=[C:16]([C:18]2[CH:19]=[N:20][N:21]([CH:23]3[CH2:24][CH2:25][N:26]([CH3:30])[CH2:27][CH2:28]3)[CH:22]=2)[N:17]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 57687060HCID 57687060, compound

Product 1

HCID 57687069HCID 57687069, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

37% Aqueous formaldehyde (0.049 ml) was added to a stirred solution 3-(1,3-benzoxazol-2-yl)-5-[1-(4-piperidyl)pyrazol-4-yl]pyrazin-2-amine (200 mg, 0.55 mmol) dissolved in methanol (2 ml) and DCM (2 ml) over a period of 5 minutes at 0° C. under an atmosphere of argon. The resulting solution was stirred at 0° C. for 5 minutes. Sodium triacetoxyborohydride (0.141 g) was added and the mixture was stirred for 5 minutes at ambient temperature. A solution of ammonia in methanol 7N (1 ml) was added and the mixture was adsorbed on silica gel. The crude product was purified by flash chromatography on silica gel (eluting with 1 to 5% methanolic ammonia (7 N) in dichloromethane). The solvent was evaporated to dryness and there was thus obtained 3-(1,3-benzoxazol-2-yl)-5-[1-(1-methyl-4-piperidyl)pyrazol-4-yl]pyrazin-2-amine (0.165 g); Mass Spectrum: M+H+ 376; NMR Spectrum (DMSOd6): 8.67 (s, 1H), 8.36 (s, 1H), 8.03 (s, 1H), 7.90 (d, 1H), 7.88 (d, 1H), 7.84 (bs, 2H), 7.51 (dd, 1H), 7.47 (dd, 1H), 4.13-4.24 (m, 1H), 2.82-2.94 (m, 2H), 2.21 (s, 3H), 1.95-2.12 (m, 6H).

Workup

  1. stirringthe mixture was stirred for 5 minutes at ambient temperature
  2. customThe crude product was purified by flash chromatography on silica gel (eluting with 1 to 5% methanolic ammonia (7 N) in dichloromethane)
  3. customThe solvent was evaporated to dryness and there

Sources & evidence

ORD record
ord-9791c9f8a72146e2b98ac377ba812a69
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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