Triethylamine → HCID 59175839, compound

HRID 1807782Notes

Reaction equation

HRID 1807782 reaction equation
[CH:1]1([CH2:4][NH:5][C:6](=[O:17])[NH:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.[F:18][C:19]([F:41])([F:40])[C:20]([C:26]1[CH:39]=[CH:38][C:29]([CH2:30][N:31]2[CH2:36][CH2:35][NH:34][CH2:33][C:32]2=[O:37])=[CH:28][CH:27]=1)([OH:25])[C:21]([F:24])([F:23])[F:22].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl>[CH:1]1([CH2:4][NH:5][C:6]([NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:12]([N:34]3[CH2:35][CH2:36][N:31]([CH2:30][C:29]4[CH:38]=[CH:39][C:26]([C:20]([OH:25])([C:19]([F:18])([F:40])[F:41])[C:21]([F:24])([F:22])[F:23])=[CH:27][CH:28]=4)[C:32](=[O:37])[CH2:33]3)=[O:14])=[CH:15][CH:16]=2)=[O:17])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 580558194-(3-(Cyclopropylmethyl)ureido)benzoic acidHCID 86638571HCID 86638571, compound

Product 1

HCID 59175839HCID 59175839, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of 4-(3-(cyclopropylmethyl)ureido)benzoic acid (0.337 mmol, 79 mg), 1-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-2-one (0.281 mmol, 100 mg) and triethylamine (0.842 mmol, 85 mg) in dichloromethane (10 ml) was added 1-propanephosphonic acid cyclic anhydride (0.421 mmol, 268 mg; 50% solution in ethyl acetate). The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with dichloromethane (20 mL) and washed with saturated aqueous sodium hydrogen carbonate solution (30 mL). The organic phase was concentrated and the resulting residue was purified by column chromatography on silica gel (eluting with 5% methanol/95% dichloromethane) to afford the title compound (36 mg). MS (ESI) m/z 573.0 [M+H]+

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution (30 mL)
  2. concentrationThe organic phase was concentrated
  3. customthe resulting residue was purified by column chromatography on silica gel (eluting with 5% methanol/95% dichloromethane)

Sources & evidence

ORD record
ord-17937476791e4218aeb927f1ad51d801
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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