Diisopropylethylamine → HCID 89872695, compound

HRID 2203147Notes

Reaction equation

HRID 2203147 reaction equation
OC([C:4]([F:7])([F:6])[F:5])=O.[CH3:8][O:9][C:10]([NH:12][C@@H:13]([CH:49]([CH3:51])[CH3:50])[C:14]([N:16]1[CH2:20][C@@H:19]([CH3:21])[CH2:18][C@H:17]1[C:22]1[NH:23][C:24]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[C:30]([C:35]4[CH:43]=[CH:42][C:38]([C:39](O)=[O:40])=[CH:37][C:36]=4[O:44]C(F)(F)F)[CH:31]=3)[C:25]=2[N:26]=1)=[O:15])=[O:11].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:76]([O:80][C:81]([N:83]1[CH2:88][CH2:87][N:86]([C:89]2[CH:94]=[CH:93][C:92]([NH2:95])=[CH:91][N:90]=2)[C@H:85]([CH3:96])[CH2:84]1)=[O:82])([CH3:79])([CH3:78])[CH3:77].CCN(C(C)C)C(C)C>CC(N(C)C)=O>[C:76]([O:80][C:81]([N:83]1[CH2:88][CH2:87][N:86]([C:89]2[CH:94]=[CH:93][C:92]([NH:95][C:39](=[O:40])[C:38]3[CH:42]=[CH:43][C:35]([C:30]4[CH:31]=[C:32]5[C:27](=[CH:28][CH:29]=4)[C:25]4[N:26]=[C:22]([C@@H:17]6[CH2:18][C@H:19]([CH3:21])[CH2:20][N:16]6[C:14](=[O:15])[C@@H:13]([NH:12][C:10]([O:9][CH3:8])=[O:11])[CH:49]([CH3:50])[CH3:51])[NH:23][C:24]=4[CH:34]=[CH:33]5)=[C:36]([O:44][C:4]([F:5])([F:6])[F:7])[CH:37]=3)=[CH:91][N:90]=2)[C@H:85]([CH3:96])[CH2:84]1)=[O:82])([CH3:79])([CH3:77])[CH3:78]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67495583HCID 67495583, compoundHCID 131732994HCID 131732994, compound

Product 1

HCID 89872695HCID 89872695, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 4-{2-[(2S,4S)-1-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-4-methyl-pyrrolidin-2-yl]-3H-naphth[1,2-d]imidazol-7-yl}-3-trifluoromethoxy-benzoic acid TFA (136 mg, 0.19 mmol; Preparation 17) and HATU (86 mg, 0.23 mmol) in DMA (3 mL) was stirred for 10 min, then (R)-4-(5-amino-pyridin-2-yl)-3-methyl-piperazine-1-carboxylic acid tert-butyl ester (55 mg, 0.19 mmol), and DIPEA (98 μL, 0.56 mmol) were added. The resulting mixture was stirred at RT for 1 h, concentrated, and purified by silica gel chromatography (EtOAc/hexane 20 to 100%) to give the title intermediate (158 mg, 95% yield). (m/z): [M+H]+ calcd for C46H53F3N8O7 887.40 found 887.4.

Workup

  1. concentrationconcentrated
  2. custompurified by silica gel chromatography (EtOAc/hexane 20 to 100%)

Sources & evidence

ORD record
ord-2b31fc87dd8d45e9b2417371a7a701a3
Source dataset
uspto-grants-2016_06
Patent number
US09365549B2

Reaction notes

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