Hydrochloric Acid → HCID 178495316, compound

HRID 2039201Notes

Reaction equation

HRID 2039201 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][S:10][CH:9]1[C:13]1[NH:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][CH:28]=[C:29]([C:34]5[N:35]=[C:36]([CH:39]6[CH2:45][C:42]7([CH2:44][CH2:43]7)[CH2:41][N:40]6[C:46](=[O:56])[CH:47]([NH:51][C:52]([O:54][CH3:55])=[O:53])[CH:48]([CH3:50])[CH3:49])[NH:37][CH:38]=5)[CH:30]=4)[CH:25]=3)=[CH:20][CH:19]=2)=[CH:16][N:17]=1)=O)(C)(C)C.Cl.CCN(C(C)C)C(C)C.[CH3:67][O:68][CH2:69][CH2:70][CH:71]([NH:75][C:76]([O:78][CH3:79])=[O:77])[C:72]([OH:74])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.O1CCOCC1.CN(C=O)C>[CH3:55][O:54][C:52](=[O:53])[NH:51][CH:47]([C:46]([N:40]1[CH:39]([C:36]2[NH:37][CH:38]=[C:34]([C:29]3[CH:28]=[CH:27][C:26]4[C:31](=[CH:32][CH:33]=[C:24]([C:21]5[CH:22]=[CH:23][C:18]([C:15]6[NH:14][C:13]([CH:9]7[N:8]([C:72](=[O:74])[CH:71]([NH:75][C:76]([O:78][CH3:79])=[O:77])[CH2:70][CH2:69][O:68][CH3:67])[CH2:12][CH2:11][S:10]7)=[N:17][CH:16]=6)=[CH:19][CH:20]=5)[CH:25]=4)[CH:30]=3)[N:35]=2)[CH2:45][C:42]2([CH2:44][CH2:43]2)[CH2:41]1)=[O:56])[CH:48]([CH3:50])[CH3:49]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 81531Diisopropylethylamine2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 624805674-Methoxy-2-methoxycarbonylamino-butyric acidHCID 178502142HCID 178502142, compound

Product 1

HCID 178495316HCID 178495316, compoundYield 39.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

2-{5-[4-(6-{2-[5-(2-Methoxycarbonylamino-3-methyl-butyryl)-5-aza-spiro[2.4]hept-6-yl]-1H-imidazol-4-yl}-naphthalen-2-yl)-phenyl]-1H-imidazol-2-yl}-thiazolidine-3-carboxylic acid tert-butyl ester (49.9 mg, 0.064 mmol) was dissolved in DCM (0.33 mL) and HCl in dioxane (4M, 0.33 mL) was added and stirring at room temperature was continued. After 45 minutes, all volatiles were removed in vacuo. The crude material was used in the next step without further purification. The crude material was dissolved in DMF (0.5 mL) and DIEA (24.6 mg, 0.191 mmol) was added. A solution of (L) 4-methoxy-2-methoxycarbonylamino-butyric acid (12.1 mg, 0.064 mmol), HATU (24.1 mg, 0.064 mmol) and DIEA (8.2 mg, 0.064 mmol) in DMF (0.5 mL) was added. The reaction was stirred at room temperature. After 3 hrs all volatiles were removed in vacuo. The crude material, which was purified by RP-HPLC (eluent: water/MeCN w/0.1% TFA) to yield the product (21.3 mg) as a TFA salt.

Workup

  1. customall volatiles were removed in vacuo
  2. customThe crude material was used in the next step without further purification
  3. dissolutionThe crude material was dissolved in DMF (0.5 mL)
  4. stirringThe reaction was stirred at room temperature
  5. customAfter 3 hrs all volatiles were removed in vacuo
  6. customThe crude material, which was purified by RP-HPLC (eluent: water/MeCN w/0.1% TFA)

Sources & evidence

ORD record
ord-7841218b442a4adcac88e8a4a09aa8d5
Source dataset
uspto-grants-2013_11
Patent number
US08575118B2

Reaction notes

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