Triethylamine → Methyl 1-(4-(3-(cyclopropylmethyl)ureido)benzoyl)-4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-2-carboxylate

HRID 1807778Notes

Reaction equation

HRID 1807778 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:44])([F:43])[C:20]([C:26]1[CH:42]=[CH:41][C:29]([CH2:30][N:31]2[CH2:36][CH2:35][NH:34][CH:33]([C:37]([O:39][CH3:40])=[O:38])[CH2:32]2)=[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](=[O:17])[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:41]=[CH:42][C:26]([C:20]([OH:25])([C:21]([F:22])([F:23])[F:24])[C:19]([F:44])([F:18])[F:43])=[CH:27][CH:28]=4)[CH2:32][CH:33]3[C:37]([O:39][CH3:40])=[O:38])=[O:14])=[CH:15][CH:16]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 580558194-(3-(Cyclopropylmethyl)ureido)benzoic acidHCID 86638569Methyl 4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-2-carboxylate

Product 1

HCID 59175829Methyl 1-(4-(3-(cyclopropylmethyl)ureido)benzoyl)-4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-2-carboxylateYield 34.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(3-(Cyclopropylmethyl)ureido)benzoic acid (0.213 mmol, 0.05 g), methyl 4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-2-carboxylate (0.213 mmol, 0.085 g) and triethylamine (0.640 mmol, 0.089 mL, 0.065 g) were combined and stirred in dichloromethane. 1-Propanephosphonic acid cyclic anhydride (0.320 mmol, 0.191 mL, 0.204 g) was added and the reaction stirred for 2 hours at room temperature. This was washed with water and the resulting residue purified by acidic prep HPLC to afford the title compound (45 mg). MS (ESI) m/z 617.2 [M+H]+

Workup

  1. washThis was washed with water
  2. customthe resulting residue purified by acidic prep HPLC

Sources & evidence

ORD record
ord-dab0bf1d5a484efe90b4180a033c3136
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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