Ammonia → HCID 67388808, compound

HRID 908488Notes

Reaction equation

HRID 908488 reaction equation
[H-].[Li+].[Al+3].[H-].[H-].[H-].[NH2:7][C:8]1[C:13]([C:14]2[O:15][C:16]3[C:22]([C:23](OC)=[O:24])=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)=[CH:12][C:11]([C:27]2[CH:28]=[N:29][N:30]([CH:32]3[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]3)[CH:31]=2)=[CH:10][N:9]=1.N>C1COCC1>[NH2:7][C:8]1[N:9]=[CH:10][C:11]([C:27]2[CH:28]=[N:29][N:30]([CH:32]3[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:42])[CH3:43])=[O:39])[CH2:34][CH2:33]3)[CH:31]=2)=[CH:12][C:13]=1[C:14]1[O:15][C:16]2[C:22]([CH2:23][OH:24])=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 21226445Aluminium lithium hydrideHCID 67388157HCID 67388157, compound

Product 1

HCID 67388808HCID 67388808, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aluminium(III) lithium hydride (0.251 ml, 1M in THF) was added dropwise to methyl 2-[2-amino-5-[1-(1-tert-butoxycarbonyl-4-piperidyl)pyrazol-4-yl]-3-pyridyl]-1,3-benzoxazole-7-carboxylate (130 mg) dissolved in THF (5 ml). 7N Methanolic ammonia (15 ml) was added to the mixture and the solution was adsorbed on silica gel and the solvent was evaporated. The crude product was purified by flash chromatography on silica gel eluting with 1 to 4% methanol in dichloromethane. The solvent was evaporated to dryness to afford tert-butyl 4-[4-[6-amino-5-[7-(hydroxymethyl)-1,3-benzoxazol-2-yl]-3-pyridyl]pyrazol-1-yl]piperidine-1-carboxylate (56.0 mg) as a clear yellow solid. NMR Spectrum: (CDCl3): 1.49 (s, 9H), 1.96 (dd, 1H), 2.00 (dd, 1H), 2.13-2.24 (m, 2H), 2.84-3.01 (m, 2H), 4.17-4.44 (m, 3H), 5.09 (s, 2H), 6.98 (bs, 2H), 7.37 (dd, 1H), 7.43 (s, 1H), 7.66 (s, 1H), 7.67 (d, 1H), 7.76 (s, 1H), 8.28 (d, 1H), 8.33 (d, 1H); Mass spectrum: M+H+ 491;

Workup

  1. customthe solvent was evaporated
  2. customThe crude product was purified by flash chromatography on silica gel eluting with 1 to 4% methanol in dichloromethane
  3. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-c39a33bad1aa4ccda10abcee1a3b9040
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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