Diisopropylethylamine → HCID 178455689, compound

HRID 2042842Notes

Reaction equation

HRID 2042842 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[Cl:23][C:24]1[C:31]([NH:32][C:33]2[NH:59][C:36]3=[N:37][C:38]([O:54][CH2:55][CH:56]([F:58])[F:57])=[C:39]([C:41](=[O:53])[NH:42][C@H:43]4[CH2:48][CH2:47][C@H:46]([C:49]([F:52])([F:51])[F:50])[CH2:45][CH2:44]4)[CH:40]=[C:35]3[N:34]=2)=[C:30]([Cl:60])[CH:29]=[CH:28][C:25]=1[CH2:26][NH2:27].CCN(C(C)C)C(C)C.[F:70][C:71]([CH3:76])([CH3:75])[C:72](O)=[O:73]>CN(C=O)C>[Cl:23][C:24]1[C:31]([NH:32][C:33]2[NH:59][C:36]3=[N:37][C:38]([O:54][CH2:55][CH:56]([F:57])[F:58])=[C:39]([C:41](=[O:53])[NH:42][C@H:43]4[CH2:48][CH2:47][C@H:46]([C:49]([F:52])([F:50])[F:51])[CH2:45][CH2:44]4)[CH:40]=[C:35]3[N:34]=2)=[C:30]([Cl:60])[CH:29]=[CH:28][C:25]=1[CH2:26][NH:27][C:72](=[O:73])[C:71]([CH3:76])([F:70])[CH3:75]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27828282-Fluoro-2-methylpropanoic acidHCID 178509821HCID 178509821, compound

Product 1

HCID 178455689HCID 178455689, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

TBTU (1.0 ml of a 0.11 M solution in DMF) is added to a mixture of 2,4-dichloro-3-[6-(trans-4-trifluoromethyl-cyclohexylcarbamoyl)-5-(2,2-difluoro-ethoxy)-3H-imidazo[4,5-b]pyridin-2-ylamino]benzylamine (1.0 ml of a 0.10 M solution in DMF), DIPEA (52 μl, 0.3 mmol) and 2-fluoro-2-methylpropionic acid (1.0 ml of a 0.13 M solution in DMF) and it is stirred for 3 d and the mixture is purified by prep. HPLC.

Workup

  1. customthe mixture is purified by prep

Sources & evidence

ORD record
ord-e80a356f7f814fa1a3967412e01586d5
Source dataset
uspto-grants-2013_11
Patent number
US08586604B2

Reaction notes

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