2,2,3,3-Tetramethylcyclopropanecarboxylic acid → HCID 86708808, compound

HRID 1751714Notes

Reaction equation

HRID 1751714 reaction equation
[NH2:1][C@H:2]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[C:3]([N:5]1[CH2:9][C@@H:8]([CH3:10])[CH2:7][C@H:6]1[C:11]1[NH:12][C:13]([C:16]2[CH:29]=[C:28]3[O:30][CH2:31][C:25]4[C:26]5[C:27]3=[C:18]([CH2:19][O:20][C:21]=5[CH:22]=[C:23]([C:32]3[NH:36][C:35]([C@@H:37]5[CH2:41][C@H:40]([CH3:42])[CH2:39][N:38]5[C:43](=[O:53])[C@@H:44]([NH:48][C:49](=[O:52])[O:50][CH3:51])[CH:45]([CH3:47])[CH3:46])=[N:34][CH:33]=3)[CH:24]=4)[CH:17]=2)=[CH:14][N:15]=1)=[O:4].[CH3:60][C:61]1([CH3:69])[C:63]([CH3:65])([CH3:64])[CH:62]1[C:66](O)=[O:67].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CCN(C(C)C)C(C)C.CN(C=O)C.O.C(O)=O.CO>[CH3:47][CH:45]([CH3:46])[C@H:44]([NH:48][C:49](=[O:52])[O:50][CH3:51])[C:43]([N:38]1[CH2:39][C@@H:40]([CH3:42])[CH2:41][C@H:37]1[C:35]1[NH:36][C:32]([C:23]2[CH:24]=[C:25]3[CH2:31][O:30][C:28]4[C:27]5=[C:18]([CH:17]=[C:16]([C:13]6[NH:12][C:11]([C@@H:6]7[CH2:7][C@H:8]([CH3:10])[CH2:9][N:5]7[C:3](=[O:4])[C@@H:2]([C:54]7[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=7)[NH:1][C:66]([CH:62]7[C:63]([CH3:65])([CH3:64])[C:61]7([CH3:69])[CH3:60])=[O:67])=[N:15][CH:14]=6)[CH:29]=4)[CH2:19][O:20][C:21]([CH:22]=2)=[C:26]35)=[CH:33][N:34]=1)=[O:53]

Participants

9

Reactant 3

HCID 1521152,2,3,3-Tetramethylcyclopropanecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86708807HCID 86708807, compound

Product 1

HCID 86708808HCID 86708808, compoundYield 50%

Reagents, catalysts & solvents 5

HCID 284Formic AcidCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 81531DiisopropylethylamineSolvent2×

Procedure

Methyl (S)-1-((2S,4S)-2-(5-(7-(2-((2S,4S)-1-((R)-2-amino-2-phenylacetyl)-4-methylpyrrolidin-2-yl)-1H-imidazol-5-yl)-5,10-dihydrochromeno[5,4,3-cde]chromen-2-yl)-1H-imidazol-2-yl)-4-methylpyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (45 mg, 0.049 mmol) in 0.5 mL 10% DIPEA in DMF was added to a mixture of 2,2,3,3-tetramethylcyclopropanecarboxylic acid (8.4 mg, 0.059 mmol) and HATU (22 mg, 0.059 mmol) in 0.2 mL 10% DIPEA in DMF. After 20 minutes stirring at room temperature, the reaction mixture was diluted with 0.2 mL water, 5 drops formic acid, and methanol to a total volume of 2.4 mL and purified by reverse phase HPLC to give 22.6 mg product as a trifluoroacetate salt.

Workup

  1. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-17fcb359c0a4466da80406cad86cba92
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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