Diisopropylethylamine → 2-{2,6-Dichloro-3-[(2-fluoro-2-methyl-propionylamino)-methyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid

HRID 1189706Notes

Reaction equation

HRID 1189706 reaction equation
[F:1][C:2]([CH3:7])([CH3:6])[C:3](O)=[O:4].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[Cl:39][C:40]1[C:45]([CH2:46][NH2:47])=[CH:44][CH:43]=[C:42]([Cl:48])[C:41]=1[NH:49][C:50]1[N:54]([CH3:55])[C:53]2[CH:56]=[C:57]([N:63]3[CH2:68][CH2:67][CH:66]([C:69]([F:72])([F:71])[F:70])[CH2:65][CH2:64]3)[C:58]([C:60]([OH:62])=[O:61])=[CH:59][C:52]=2[N:51]=1>CN(C=O)C>[Cl:39][C:40]1[C:45]([CH2:46][NH:47][C:3](=[O:4])[C:2]([F:1])([CH3:7])[CH3:6])=[CH:44][CH:43]=[C:42]([Cl:48])[C:41]=1[NH:49][C:50]1[N:54]([CH3:55])[C:53]2[CH:56]=[C:57]([N:63]3[CH2:68][CH2:67][CH:66]([C:69]([F:72])([F:71])[F:70])[CH2:65][CH2:64]3)[C:58]([C:60]([OH:62])=[O:61])=[CH:59][C:52]=2[N:51]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27828282-Fluoro-2-methylpropanoic acidHCID 679573152-{2,6-Dichloro-3-[aminomethyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid

Product 1

HCID 866664932-{2,6-Dichloro-3-[(2-fluoro-2-methyl-propionylamino)-methyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 2-fluoroisobutyric acid (191 mg, 1.80 mmol), TBTU (578 mg, 1.80 mmol), DIPEA (1.00 mL, 5.7 mmol) and 10 mL DMF is stirred for 10 min and then the mixture is added to 2-{2,6-dichloro-3-[aminomethyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid (929 mg, 1.80 mmol) in 10 mL DMF and it is stirred overnight. Then the mixture is concentrated and purified via prep HPLC.

Workup

  1. stirringis stirred overnight
  2. concentrationThen the mixture is concentrated
  3. custompurified via prep HPLC

Sources & evidence

ORD record
ord-f3bad27079534488879a782be23cc20a
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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