Hydrochloric Acid → HCID 178502422, compound

HRID 1751342Notes

Reaction equation

HRID 1751342 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:52]([CH3:54])[CH3:53])[C:7]([N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]1[NH:15][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:26]=[C:27]4[C:49](=[CH:50][CH:51]=3)[C:31]3[NH:32][C:33]([C@@H:35]5[C@@H:40]6[CH2:41][C@@H:37]([CH2:38][CH2:39]6)[N:36]5C(OC(C)(C)C)=O)=[N:34][C:30]=3[CH:29]=[CH:28]4)=[CH:21][CH:20]=2)=[CH:17][N:18]=1)=[O:8])=[O:4].Cl.[CH3:56][O:57][C@H:58]([CH3:68])[C@H:59]([NH:63][C:64]([O:66][CH3:67])=[O:65])[C:60]([OH:62])=O.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>[CH3:56][O:57][C@H:58]([CH3:68])[C@H:59]([NH:63][C:64](=[O:65])[O:66][CH3:67])[C:60]([N:36]1[C@H:35]([C:33]2[NH:32][C:31]3[C:49]4[C:27]([CH:28]=[CH:29][C:30]=3[N:34]=2)=[CH:26][C:25]([C:22]2[CH:21]=[CH:20][C:19]([C:16]3[NH:15][C:14]([C@@H:10]5[CH2:11][CH2:12][CH2:13][N:9]5[C:7](=[O:8])[C@@H:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[CH:52]([CH3:54])[CH3:53])=[N:18][CH:17]=3)=[CH:24][CH:23]=2)=[CH:51][CH:50]=4)[C@@H:40]2[CH2:41][C@H:37]1[CH2:38][CH2:39]2)=[O:62]

Participants

8

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 59540170(2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoic acidHCID 178502423HCID 178502423, compound

Product 1

HCID 178502422HCID 178502422, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To (1R,3S,4S)-tert-butyl 3-(7-(4-(2-((S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl) pyrrolidin-2-yl)-1H-imidazol-5-yl)phenyl)-1H-naphtho[1,2-d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate (280 mg, 0.38 mmol) in DCM (5 mL) was added HCl (4M in dioxane, 1 mL). The solution stirred for 2 h, and the solvent was removed. The intermediate (80 mg, 0.13 mmol) was dissolved in DMF (2 mL). (2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoic acid (24 mg, 0.13 mmol), HATU (48 mg, 0.13 mmol), and DIPEA (0.11 mL, 0.64 mmol) were added sequentially. The solution stirred o/n and the mixture was purified by HPLC to yield product (54.6 mg). LCMS-ESI+: calc'd for C44H52N8O7: 804.93 (M+); Found: 806.23 (M+H+).

Workup

  1. customthe solvent was removed
  2. stirringThe solution stirred o/n and the mixture
  3. customwas purified by HPLC

Sources & evidence

ORD record
ord-fd9831c1e5d741d3b56c181bdff36aa9
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

Loading…