Trifluoroacetic acid → HCID 66967104, compound

HRID 1711932Notes

Reaction equation

HRID 1711932 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][C:19](=[O:21])[NH:18][C:17]2[CH:22]=[C:23](/[CH:26]=[CH:27]/[C:28](=[O:42])[N:29]([CH3:41])[CH2:30][C:31]3[N:32]([CH3:40])[C:33]4[C:38]([CH:39]=3)=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH:24]=[N:25][C:16]1=2)=O)(C)(C)C>C(Cl)Cl>[CH3:41][N:29]([CH2:30][C:31]1[N:32]([CH3:40])[C:33]2[C:38]([CH:39]=1)=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:28](=[O:42])/[CH:27]=[CH:26]/[C:23]1[CH:24]=[N:25][C:16]2[NH:15][CH2:20][C:19](=[O:21])[NH:18][C:17]=2[CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66966526HCID 66966526, compound

Product 1

HCID 66967104HCID 66967104, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.5 mL) was added to a solution of (E)-7-{2-[methyl-(1-methyl-1H-indol-2-ylmethyl)-carbamoyl]-vinyl}-2-oxo-2,3-dihydro-1H-pyrido[2,3-b]pyrazine-4-carboxylic acid tert-butyl ester in CH2Cl2 (1 mL) at 10° C. After stirring 1 hr, volatiles were removed in vacuo and the resulting residue was dissolved in EtOAc (2 mL). Upon addition of dilute NaOH, a precipitate formed. The solid was collected by filtration, washed with water (100 mL), MeOH (50 mL), EtOAc (50 mL) and CH2Cl2 (50 mL) to afford the title compound (170 mg). 1H NMR (300 MHz, DMSO-d6) δ 10.42 and 10.33 (rotamers, 2s, br, 1H), 7.90 (m, 1H), 7.45 (m, 3H), 7.22 (m, 1H), 7.12 (m, 1H), 6.83 (d, J=15.4 Hz, 1H), 6.42 and 6.17 (rotamers, 2s, 1H), 4.98 and 4.84 (rotamers, 2s, 2H), 3.99 and 3.95 (rotamers, 2s, 2H), 3.72 and 3.68 (rotamers, 2s, 3H), 3.07 and 3.00 (rotamers, 2s, 3H). MS (ESI) m/e: 376 (M+H)+.

Workup

  1. customvolatiles were removed in vacuo
  2. dissolutionthe resulting residue was dissolved in EtOAc (2 mL)
  3. additionUpon addition of dilute NaOH
  4. customa precipitate formed
  5. filtrationThe solid was collected by filtration
  6. washwashed with water (100 mL), MeOH (50 mL), EtOAc (50 mL) and CH2Cl2 (50 mL)

Sources & evidence

ORD record
ord-f2963ec1970b469796a71123ae566752
Source dataset
uspto-grants-2010_09
Patent number
US07790709B2

Reaction notes

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