Hydrochloric Acid → HCID 9807740, compound

HRID 1736422Notes

Reaction equation

HRID 1736422 reaction equation
CC(C)(OC([N:7]([CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][S:29]([C:32]2[CH:37]=[CH:36][C:35]([NH:38][C:39]([NH:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[O:40])=[CH:34][CH:33]=2)(=[O:31])=[O:30])=[CH:24][CH:23]=1)[CH2:8][C@H:9]([OH:19])[C:10]1[CH:11]=[CH:12][C:13]2[N:14](N=N[N:18]=2)[CH:15]=1)=O)C.O.O.[Sn](Cl)Cl.Cl>CO>[OH:19][C@H:9]([C:10]1[CH:15]=[N:14][C:13]([NH2:18])=[CH:12][CH:11]=1)[CH2:8][NH:7][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][S:29]([C:32]2[CH:37]=[CH:36][C:35]([NH:38][C:39]([NH:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[O:40])=[CH:34][CH:33]=2)(=[O:31])=[O:30])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 15294255HCID 15294255, compound

Product 1

HCID 9807740HCID 9807740, compoundYield 131.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.302 g (0.44 mmol) of the tetrazine from Example 4, 0.20 g (0.88 mol) of tin(II) chloride dihydrate and 0.3 ml of concentrated aqueous hydrochloric acid in 2 mL of methanol was heated at reflux for 5 h. The reaction mixture was concentrated and the residue purified by reverse-phase MPLC (C8, 47%methanol/53 0.1% trifluoroacetic acid buffer) to give 0.32 g (78%) of the title compound as its bistrifluoroacetate salt: 1H NMR (400 MHz, CD3OD) δ7.96 (dd, 1H, J=2.0, 9.2 Hz), 7.86 (d, 1H, J=2.0 Hz), 7.59 (d, 2H, J=8.8 Hz), 7.43 (d, 2H, J=8.8 Hz), 7.14 (d, 2H, J=8.4 Hz), 7.07 (d, 2H, J=8.4 Hz), 7.03 (d, 1H, J=9.2 Hz), 4.92 (m, 1H), 3.23 (m, 2H), 3.15 (m, 2H), 2.93 (m, 2H, 4.0 Hz), 1.49 (t, 2H, J=6.0 Hz), 1.32 (m, 8H), 0.91 (t, 3H, J=6.0 Hz); CI MS m/z 555(M+1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 h
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue purified by reverse-phase MPLC (C8, 47%methanol/53 0.1% trifluoroacetic acid buffer)

Sources & evidence

ORD record
ord-0934c63e480f411083d35e61e99e45ac
Source dataset
uspto-grants-1996_07
Patent number
US05541197

Reaction notes

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