Trifluoroacetic acid → HCID 66867193, compound

HRID 254010Notes

Reaction equation

HRID 254010 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][CH2:11][N:12](C(OC(C)(C)C)=O)[CH2:13][CH:14]=2)=[CH:4][C:3]=1[C:22]1[N:26]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:28]=2[F:34])[N:25]=[N:24][N:23]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:34][C:28]1[C:29]([F:33])=[CH:30][CH:31]=[CH:32][C:27]=1[N:26]1[C:22]([C:3]2[C:2]([NH2:1])=[N:7][CH:6]=[C:5]([C:8]3=[CH:14][CH2:13][NH:12][CH2:11][CH2:10][CH2:9]3)[CH:4]=2)=[N:23][N:24]=[N:25]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58179868HCID 58179868, compound

Product 1

HCID 66867193HCID 66867193, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-tert-Butyl 5-(6-amino-5-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)pyridin-3-yl)-3,4-dihydro-2H-azepine-1(7H)-carboxylate (14 mg, 29.9 μmol, 1 eq.) was diluted in 1:1 TFA:DCM (1.5 mL) and the mixture stirred at room temperature for 2 hours. The reaction was concentrated and purified by reversed-phase HPLC purification to give 3-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)-5-((E)-2,5,6,7-tetrahydro-1H-azepin-4-yl)pyridin-2-amine in quantitative yield; 1H NMR (300 MHz, DMSO-d6): 9.0 (br s, 2H); 8.25 (m, 1H); 7.87-7.77 (m, 1H); 7.75-7.6 (m, 2H); 7.6-4.5 (m, 1H); 5.85 (m, 1H); 3.7 (m, 2H); 3.25 (m, 2H); 2.5 (m, 2H); 1.78 (m, 2H).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by reversed-phase HPLC purification

Sources & evidence

ORD record
ord-ae7570a3899841fb8908d0ce67be663f
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

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