Dimethylformamide → HCID 178425017, compound

HRID 2090550Notes

Reaction equation

HRID 2090550 reaction equation
Cl.[NH:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]1[NH:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]4[N:26]=[C:27]([C@@H:30]5[CH2:34][CH2:33][CH2:32][NH:31]5)[NH:28][CH:29]=4)[CH:20]=3)=[CH:14][CH:13]=2)=[CH:10][N:11]=1.[CH:35](N(CC)C(C)C)([CH3:37])[CH3:36].CN(C(ON1N=N[C:54]2[CH:55]=[CH:56][CH:57]=N[C:53]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:68]1([CH3:78])[CH:73]=[CH:72][CH:71]=[C:70]([CH2:74][C:75]([OH:77])=O)[CH:69]=1.CN([CH:82]=[O:83])C>>[C:54]1([CH3:53])[CH:55]=[CH:56][CH:57]=[C:35]([CH2:37][C:82]([N:2]2[CH2:6][CH2:5][CH2:4][C@H:3]2[C:7]2[NH:8][C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]5[N:26]=[C:27]([C@@H:30]6[CH2:34][CH2:33][CH2:32][N:31]6[C:75](=[O:77])[CH2:74][C:70]6[CH:69]=[C:68]([CH3:78])[CH:73]=[CH:72][CH:71]=6)[NH:28][CH:29]=5)[CH:20]=4)=[CH:14][CH:13]=3)=[CH:10][N:11]=2)=[O:83])[CH:36]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 12121m-Tolylacetic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178478256HCID 178478256, compound

Product 1

HCID 178425017HCID 178425017, compound

Procedure

To a solution of 2-((S)-pyrrolidin-2-yl)-5-(4-(3-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-4-yl)phenoxy)phenyl)-1H-imidazole hydrochloride (100 mg, 0.22 mmol) in DMF (22 mL) was added N,N-diisopropylethylamine (0.2 mL), HATU (216 mg, 0.56 mmol) and 2-m-tolyl acetic acid (75 mg, 0.5 mmol). The reaction was stirred for 1 hour at room temperature and concentrated under reduced pressure. The crude product was purified by reverse-phase preparative HPLC to provide 2-m-tolyl-1-((2S)-2-(5-(4-(3-(2-((S)-1-(2-m-tolylacetyl)pyrrolidin-2-yl)-1H-imidazol-4-yl)phenoxy)phenyl)-1H-imidazol-2-yl)pyrrolidin-1-yl)ethanone (5 mg).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude product was purified by reverse-phase preparative HPLC

Sources & evidence

ORD record
ord-7b6b3585289e454e9d6dcf228e0f0418
Source dataset
uspto-grants-2013_05
Patent number
US08436036B2

Reaction notes

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