Potassium Carbonate → HCID 42599841, compound

HRID 908491Notes

Reaction equation

HRID 908491 reaction equation
Cl[CH2:2][C:3]([NH:5][CH3:6])=[O:4].[O:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[C:16]1[C:17]([NH2:36])=[N:18][CH:19]=[C:20]([C:22]2[C:23]([CH2:33][O:34][CH3:35])=[N:24][N:25]([CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[CH:26]=2)[CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:36][C:17]1[N:18]=[CH:19][C:20]([C:22]2[C:23]([CH2:33][O:34][CH3:35])=[N:24][N:25]([CH:27]3[CH2:28][CH2:29][N:30]([CH2:2][C:3]([NH:5][CH3:6])=[O:4])[CH2:31][CH2:32]3)[CH:26]=2)=[CH:21][C:16]=1[C:8]1[O:7][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 667732-chloro-N-methylacetamideHCID 673881403-(1,3-Benzoxazol-2-yl)-5-[3-(methoxymethyl)-1-(4-piperidyl)pyrazol-4-yl]pyridin-2-amine

Product 1

HCID 42599841HCID 42599841, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
75 °C

Procedure

A solution of 2-chloro-N-methyl-acetamide (0.027 ml) in DMF (1 ml) was added to a stirred mixture of 3-(1,3-benzoxazol-2-yl)-5-[3-(methoxymethyl)-1-(4-piperidyl)pyrazol-4-yl]pyridin-2-amine (100 mg) and potassium carbonate (68 mg) in DMF (5 ml) at 25° C. under argon. The resulting solution was heated at 75° C. overnight. The DMF was evaporated and the residue was purified by preparative HPLC using a Waters X-Bridge reverse-phase column (5 microns silica, 30 mm diameter, 150 mm length) and decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. The fractions were evaporated to afford 2-[4-[4-[6-amino-5-(1,3-benzoxazol-2-yl)-3-pyridyl]-3-(methoxymethyl)pyrazol-1-yl]-1-piperidyl]-N-methyl-acetamide (53.0 mg) as a solid. NMR Spectrum: (DMSOd6) 1.98-2.06 (m, 2H), 2.09 (dd, 1H), 2.14 (dd, 1H), 2.22-2.31 (m, 2H), 2.64 (d, 3H), 2.86-2.93 (m, 2H), 2.95 (s, 2H), 3.41 (s, 3H), 4.11-4.19 (m, 1H), 4.41 (s, 2H), 7.41-7.48 (m, 2H), 7.66 (bs, 2H), 7.75 (q, 1H), 7.78 (dd, 1H), 7.84 (dd, 1H), 8.19 (s, 1H), 8.43 (d, 1H), 8.50 (d, 1H); Mass spectrum: M+H+ 476.

Workup

  1. customThe DMF was evaporated
  2. customthe residue was purified by preparative HPLC
  3. customThe fractions were evaporated

Sources & evidence

ORD record
ord-cdde497c492d4c94857a48626dd73376
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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