Trifluoroacetic acid → HCID 178487623, compound

HRID 20703Notes

Reaction equation

HRID 20703 reaction equation
C([NH:8][C:9]([N:18]1[CH:22]=[CH:21][CH:20]=N1)=[N:10]C(OC(C)(C)C)=O)(OC(C)(C)C)=O.NCCC[CH2:27][CH2:28][O:29][C:30]1[C:31]([O:50][CH3:51])=[CH:32][CH:33]=[C:34]2[C:39]=1[O:38][C:37](=[O:40])[CH:36]=[C:35]2[NH:41][C:42]1[C:47]([Cl:48])=[CH:46][N:45]=[CH:44][C:43]=1[Cl:49].FC(F)(F)C(O)=O>ClCCl>[Cl:49][C:43]1[CH:44]=[N:45][CH:46]=[C:47]([Cl:48])[C:42]=1[NH:41][C:35]1[C:34]2[C:39](=[C:30]([O:29][CH2:28][CH2:27][CH2:20][CH2:21][CH2:22][NH:18][C:9]([NH2:8])=[NH:10])[C:31]([O:50][CH3:51])=[CH:32][CH:33]=2)[O:38][C:37](=[O:40])[CH:36]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 4428040N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidineHCID 248498868-(5-Aminopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one

Product 1

HCID 178487623HCID 178487623, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N′-Di-Boc-1H-pyrazole-1-carboxamidine (40 mg, 0.13 mmol) was added to a mixture of 8-(5-aminopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one (40 mg, 0.09 mmol, Example 68) and dichloromethane (3 mL). After stirring for 30 min, trifluoroacetic acid (0.3 mL) was added. After an additional 19 h, the reaction was concentrated and purified by reverse-phase HPLC (1:9→3:2; acetonitrile:water) to give to give 1-(5-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)pentyl)guanidine: 1H NMR (400 MHz, DMSO-d6; HCl salt): δ 9.60 (s, 1H), 8.82 (s, 2H), 7.98 (d, 1H), 7.57 (t, 1H), 7.50-6.70 (br, 4H), 7.21 (d, 1H), 4.63 (s, 1H), 3.98 (t, 2H), 3.92 (s, 3H), 3.11 (m, 2H), 1.70 (m, 2H), 1.52 (m, 4H); MS (ESI): 479.9.

Workup

  1. waitAfter an additional 19 h
  2. concentrationthe reaction was concentrated
  3. custompurified by reverse-phase HPLC (1:9→3:2; acetonitrile:water)
  4. customto give

Sources & evidence

ORD record
ord-542c2b3b218c4b90895df7cd7c66887d
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Reaction notes

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