Sodium Carbonate → HCID 68378994, compound

HRID 2038778Notes

Reaction equation

HRID 2038778 reaction equation
[C:1]([NH:8][C@H:9]([C:11]([OH:13])=O)[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.Cl.[NH:40]1[CH:44]=[C:43]([C:45]2[N:50]=[N:49][C:48]([C:51]3([NH2:54])[CH2:53][CH2:52]3)=[CH:47][CH:46]=2)[CH:42]=[N:41]1.C(N(C(C)C)CC)(C)C.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:4]([O:3][C:1](=[O:2])[NH:8][C@H:9]([C:11](=[O:13])[NH:54][C:51]1([C:48]2[N:49]=[N:50][C:45]([C:43]3[CH:44]=[N:40][NH:41][CH:42]=3)=[CH:46][CH:47]=2)[CH2:52][CH2:53]1)[CH3:10])([CH3:5])([CH3:6])[CH3:7]

Participants

7

Reactant 5

HCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 85082Tert-butoxycarbonylalanineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67514828HCID 67514828, compound

Product 1

HCID 68378994HCID 68378994, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the N-Boc-alanine (89 mg, 0.48 mmol), HATU (199 mg, 0.52 mmol), and 1-[6-(1H-pyrazol-4-yl)-pyridazin-3-yl]-cyclopropylamine dihydrochloride (130 mg, 0.48 mmol) in CH2Cl2 (1.9 mL) was added diisopropylethylamine (0.33 mL, 1.9 mmol). The brown mixture was stirred for 2 h then 10% (w/w) aqueous Na2CO3 (5 mL) was added and stirring continued for 20 min. The layers were separated and the aqueous layer was extracted with CH2Cl2 (2×5 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated to afford a brown oil. This was purified via normal phase flash chromatography on silica gel (1→20% MeOH/CH2Cl2) to yield mg of ((S)-1-{1-[6-(1H-pyrazol-4-yl)-pyridazin-3-yl]-cyclopropylcarbamoyl}-ethyl)-carbamic acid tert-butyl ester, m/z 373.7 [M+H]+.

Workup

  1. stirringstirring
  2. waitcontinued for 20 min
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (2×5 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a brown oil
  9. customThis was purified via normal phase flash chromatography on silica gel (1→20% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-a1794bcd337b4db881a380b37a112ab2
Source dataset
uspto-grants-2013_11
Patent number
US08575360B2

Reaction notes

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