Hydrochloric Acid → HCID 67681755, compound

HRID 1751348Notes

Reaction equation

HRID 1751348 reaction equation
[CH3:1][C:2]1([CH3:42])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[C:11]3[C:23]4[C:24]5[C:14](=[CH:15][C:16]([C:25]6[NH:29][C:28]([C@@H:30]7[CH2:34][CH2:33][CH2:32][N:31]7C(OC(C)(C)C)=O)=[N:27][CH:26]=6)=[CH:17][C:18]=5[CH2:19][CH2:20][C:21]=4[CH:22]=2)[CH2:13][CH2:12]3)[O:3]1.Cl.[CH3:44][O:45][C:46]([NH:48][C@@H:49]([CH:53]([CH3:55])[CH3:54])[C:50]([OH:52])=O)=[O:47].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>C(Cl)Cl.CN(C=O)C.CCOC(C)=O>[CH3:54][CH:53]([CH3:55])[C@H:49]([NH:48][C:46](=[O:47])[O:45][CH3:44])[C:50](=[O:52])[N:31]1[CH2:32][CH2:33][CH2:34][C@H:30]1[C:28]1[NH:29][C:25]([C:16]2[CH:15]=[C:14]3[C:24]4[C:23]5[C:11]([CH2:12][CH2:13]3)=[CH:10][C:9]([B:4]3[O:5][C:6]([CH3:8])([CH3:7])[C:2]([CH3:42])([CH3:1])[O:3]3)=[CH:22][C:21]=5[CH2:20][CH2:19][C:18]=4[CH:17]=2)=[CH:26][N:27]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acidHCID 69675487HCID 69675487, compound

Product 1

HCID 67681755HCID 67681755, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To (S)-tert-butyl 2-(5-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,5,9,10-tetrahydropyren-2-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (300 mg, 0.53 mmol) in DCM (5 mL) was added HCl (4M in dioxane, 1 mL). The solution stirred for 1 h, and the solvent was removed. The intermediate (247 mg, 0.53 mmol) was dissolved in DMF (5 mL). (S)-2-(methoxycarbonylamino)-3-methylbutanoic acid (93 mg, 0.53 mmol), HATU (200 mg, 0.53 mmol), and DIPEA (0.46 mL, 2.65 mmol) were added sequentially. The solution was stirred o/n. The mixture was diluted with EtOAc, and washed with sat. NaHCO3, brine, dried with MgSO4, and concentrated, and the mixture was purified by silica gel chromatography to yield product (139 mg).

Workup

  1. customthe solvent was removed
  2. stirringThe solution was stirred o/n
  3. washwashed with sat. NaHCO3, brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customthe mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1245d067d27148f8a689cc72853a6998
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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