Trifluoroacetic acid → RUC-4

HRID 624680Notes

Reaction equation

HRID 624680 reaction equation
C(OC([NH:8][CH2:9][C:10]([NH:12][C:13]1[CH:14]=[C:15]([C:19]2[S:41][C:22]3=[N:23][C:24]([N:28]4[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]4)=[CH:25][C:26](=[O:27])[N:21]3[N:20]=2)[CH:16]=[N:17][CH:18]=1)=[O:11])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH2:9][C:10]([NH:12][C:13]1[CH:18]=[N:17][CH:16]=[C:15]([C:19]2[S:41][C:22]3=[N:23][C:24]([N:28]4[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]4)=[CH:25][C:26](=[O:27])[N:21]3[N:20]=2)[CH:14]=1)=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89711480HCID 89711480, compound

Product 1

HCID 71668132RUC-4

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(2-(5-(2-(tert-butoxycarbonylamino)acetamido)pyridin-3-yl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate (20 mg, 0.034 mmol) in DCM (2 ml) is added TFA (0.5 ml). The mixture is stirred for 2 h, concentrated in vacuo and the residue is directly purified by preparative HPLC to give the desired product 2-Amino-N-(5-(5-oxo-7-(piperazin-1-yl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-2-yl)pyridin-3-yl)acetamide: 1H NMR (400 MHz, DMSO-d6) δ 11.11 (s, 1H), 9.10-8.90 (br.s., 2H), 8.94 (d, J=2.0 Hz, 1H), 8.83 (d, J=2.0 Hz, 1H), 8.67 (t, J=2.0 Hz, 1H), 8.35-8.15 (br.s., 3H), 5.62 (s, 1H), 3.89 (s, 2H), 3.85 (t, J=5.2 Hz, 4H), 3.20 (t, J=5.2 Hz, 4H); LC/MS: tR=1.908 min; HRMS: m/z (M+H+)=387.1344 (Calculated for C16H19N8O2S=387.1352).

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue is directly purified by preparative HPLC

Sources & evidence

ORD record
ord-83996f4a56044a2aa455fee9deca723f
Source dataset
uspto-grants-2016_04
Patent number
US09303044B2

Reaction notes

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