Propylphosphoric anhydride → HCID 178501909, compound

HRID 405855Notes

Reaction equation

HRID 405855 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][N:9]3[C:12]([C:15]([OH:17])=O)=[CH:13][N:14]=[C:8]3[CH:7]=2)=[N:2]1.[NH2:18][C:19]1[CH:20]=[C:21]([C:26]2[N:30]=[C:29]([CH:31]3[CH2:34][N:33]([C:35]([O:37][CH3:38])=[O:36])[CH2:32]3)[O:28][N:27]=2)[CH:22]=[CH:23][C:24]=1[CH3:25].CCCP(=O)=O>C(OCC)(=O)C>[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][N:9]3[C:12]([C:15]([NH:18][C:19]4[CH:20]=[C:21]([C:26]5[N:30]=[C:29]([CH:31]6[CH2:34][N:33]([C:35]([O:37][CH3:38])=[O:36])[CH2:32]6)[O:28][N:27]=5)[CH:22]=[CH:23][C:24]=4[CH3:25])=[O:17])=[CH:13][N:14]=[C:8]3[CH:7]=2)=[N:2]1

Participants

5

Reactant 3

HCID 16167369Propylphosphoric anhydrideHCID 86677444Methyl 3-(3-(3-amino-4-methylphenyl)-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylateHCID 178524703HCID 178524703, compound

Product 1

HCID 178501909HCID 178501909, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
80 °C

Procedure

To a stirring solution of 7-(1H-pyrazol-3-yl)imidazo[1,2-a]pyridine-3-carboxylic acid (63) (31.7 mg, 0.14 mmol), and methyl (3-(3-amino-4-methylphenyl)-1,2,4-oxadiazol-5-yl)methylcarbamate (31) (52 mg, 0.18 mmol) in ethyl acetate (0.1 mL) was added propylphosphonic anhydride (50 wt % in ethyl acetate 0.41 mL). The reaction was heated at 80° C. for 12 hours. The resulting mixture was diluted in ethyl acetate and washed with 1N Na2CO3. After aqueous workup, the residue was purified by reverse phase HPLC to afford methyl 3-(3-(3-(7-(1H-pyrazol-3-yl)imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate (F68). MS (m/z) 499.1 (M+1)+.

Workup

  1. washwashed with 1N Na2CO3
  2. customAfter aqueous workup, the residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-319f3770da184255911f724e5c38ea81
Source dataset
uspto-grants-2014_06
Patent number
US08754071B2

Reaction notes

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