Hydrochloric Acid → HCID 178502312, compound

HRID 1751354Notes

Reaction equation

HRID 1751354 reaction equation
C(OC([N:8]1[C@H:13]([C:14]2[NH:18][C:17]3[C:19]4[C:24]([CH2:25][CH2:26][C:16]=3[N:15]=2)=[CH:23][C:22]([C:27]2[CH:28]=[C:29]3[C:53](=[CH:54][CH:55]=2)[C:33]2[NH:34][C:35]([C@@H:37]5[CH2:41][CH2:40][CH2:39][N:38]5[C:42](=[O:52])[C@@H:43]([NH:47][C:48]([O:50][CH3:51])=[O:49])[CH:44]([CH3:46])[CH3:45])=[N:36][C:32]=2[CH:31]=[CH:30]3)=[CH:21][CH:20]=4)[C@@H:12]2[CH2:56][C@H:9]1[CH2:10][CH2:11]2)=O)(C)(C)C.Cl.[CH3:58][O:59][C:60]([NH:62][C@@H:63]([CH:67]1[CH2:72][CH2:71][O:70][CH2:69][CH2:68]1)[C:64]([OH:66])=O)=[O:61].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.CO.CN(C=O)C>[CH3:51][O:50][C:48]([NH:47][C@@H:43]([CH:44]([CH3:46])[CH3:45])[C:42]([N:38]1[CH2:39][CH2:40][CH2:41][C@H:37]1[C:35]1[NH:34][C:33]2[C:53]3[C:29]([CH:30]=[CH:31][C:32]=2[N:36]=1)=[CH:28][C:27]([C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[C:17]1[NH:18][C:14]([C@@H:13]4[C@@H:12]5[CH2:56][C@@H:9]([CH2:10][CH2:11]5)[N:8]4[C:64](=[O:66])[C@@H:63]([NH:62][C:60](=[O:61])[O:59][CH3:58])[CH:67]4[CH2:72][CH2:71][O:70][CH2:69][CH2:68]4)=[N:15][C:16]=1[CH2:26][CH2:25]2)=[CH:55][CH:54]=3)=[O:52])=[O:49]

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 59264488(S)-2-(Methoxycarbonylamino)-2-(tetrahydro-2H-pyran-4-yl)acetic acidHCID 178502313HCID 178502313, compound

Product 1

HCID 178502312HCID 178502312, compoundYield 58.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To (1R,3S,4S)-tert-butyl-3-(2′-((S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)pyrrolidin-2-yl)-4,5-dihydro-1H,1′H-7,7′-binaphtho[1,2-d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate (307 mg, 0.41 mmol) in DCM (5 mL) and MeOH (1 mL) was added HCl (4M in dioxane, 1 mL). The solution stirred for 2 h, and the solvent was removed. The intermediate (133 mg, 0.2 mmol) was dissolved in DMF (2.5 mL). ((S)-2-(methoxycarbonylamino)-2-(tetrahydro-2H-pyran-4-yl)acetic acid (43 mg, 0.2 mmol), HATU (76 mg, 0.2 mmol), and DIPEA (0.18 mL, 1.0 mmol) were added sequentially. The solution stirred o/n and the mixture was purified by HPLC to yield product (100.8 mg). LCMS-ESI+: calc'd for C48H56N8O7: 857.01 (M+); Found: 857.42 (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-5c86638edee345d3b91db0e3b3ea9bd1
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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