Trifluoroacetic acid → HCID 67050708, compound

HRID 886134Notes

Reaction equation

HRID 886134 reaction equation
[F:1][C:2]([F:27])([F:26])[CH2:3][N:4]1[C:8]([C:9]2[CH:10]=[C:11]3[N:17]([N:18]=2)[C:16]2[CH:19]=[C:20]([C:23]([OH:25])=O)[CH:21]=[CH:22][C:15]=2[O:14][CH2:13][CH2:12]3)=[N:7][CH:6]=[N:5]1.C(OC([N:35]1[CH:39]=[C:38]([NH2:40])[CH:37]=[N:36]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:35]1[CH:39]=[C:38]([NH:40][C:23]([C:20]2[CH:21]=[CH:22][C:15]3[O:14][CH2:13][CH2:12][C:11]4[N:17]([N:18]=[C:9]([C:8]5[N:4]([CH2:3][C:2]([F:1])([F:27])[F:26])[N:5]=[CH:6][N:7]=5)[CH:10]=4)[C:16]=3[CH:19]=2)=[O:25])[CH:37]=[N:36]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 58205012HCID 58205012, compoundHCID 59587648tert-butyl 4-amino-1H-pyrazole-1-carboxylate

Product 1

HCID 67050708HCID 67050708, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure for 126, 2-[2-(2,2,2-trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-1,10b-diaza-benzo[e]azulene-9-carboxylic acid was reacted with 4-amino-pyrazole-1-carboxylic acid tert-butyl ester. The intermediate carboxylic acid tert-butyl ester was dissolved in DCM (5 mL) and treated with TFA (2 mL) before the reaction mixture was stirred at RT for 2 h. The reaction mixture was concentrated in vacuo and the resultant residue triturated in water to give 127 as a white solid. 1H NMR (DMSO-d6, 400 MHz): δ 10.53 (s, 1H); 8.51 (d, J=2.2 Hz, 1H); 8.23 (s, 1H); 7.96 (dd, J=8.5, 2.2 Hz, 1H); 7.84 (s, 2H); 7.39 (d, J=8.5 Hz, 1H); 7.02 (s, 1H); 5.77 (q, J=8.7 Hz, 2H); 4.59 (t, J=5.8 Hz, 2H). 3 Protons obscured by water peak. LCMS: RT=9.11 min, M+H+=445

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resultant residue triturated in water

Sources & evidence

ORD record
ord-835d49e6ed854b1abd531cda2800811a
Source dataset
uspto-grants-2012_08
Patent number
US08242104B2

Reaction notes

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