Trifluoroacetic acid → 2-amino-N-[4-(5-oxo-7-piperazin-1-yl-[1,3,4]thiadiazolo[3,2-a]pyrimidin-2-yl)-2-pyridinyl]acetamide

HRID 624678Notes

Reaction equation

HRID 624678 reaction equation
C(OC([NH:8][CH2:9][C:10]([NH:12][C:13]1[CH:18]=[C:17]([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]=[CH:15][N:14]=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]=[C:17]([C:19]2[S:41][C:22]3=[N:23][C:24]([N:28]4[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]4)=[CH:25][C:26](=[O:27])[N:21]3[N:20]=2)[CH:16]=[CH:15][N:14]=1)=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89711461tert-butyl 4-(2-(2-(2-((tert-butoxycarbonyl)amino)acetamido)pyridin-4-yl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate

Product 1

HCID 716211702-amino-N-[4-(5-oxo-7-piperazin-1-yl-[1,3,4]thiadiazolo[3,2-a]pyrimidin-2-yl)-2-pyridinyl]acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(2-(2-(2-((tert-butoxycarbonyl)amino)acetamido)pyridin-4-yl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate (50 mg, 0.085 mmol) in DCM (1 ml) is added TFA (0.25 ml) and the mixture is stirred at room temperature for 2 h. The solvent is removed in vacuo and the residue is directly purified through preparative HPLC to give the desired 2-Amino-N-(4-(5-oxo-7-(piperazin-1-yl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-2-yl)pyridin-2-yl)acetamide. 1H NMR (400 MHz, DMSO-d6) δ 11.31 (s, 1H), 9.10-8.60 (br.s., 2H), 8.61 (d, J=5.1 Hz, 1H), 8.58 (s, 1H), 8.35-8.05 (br.s., 3H), 7.66 (dd, J=5.1, 1.6 Hz, 1H), 5.63 (s, 1H), 3.92 (s, 2H), 3.79 (t, J=4.7 Hz, 4H), 3.19 (t, J=4.7 Hz, 4H); LC/MS: tR=2.163 min; HRMS: m/z (M+H+)=387.1346 (Calculated for C16H19N8O2S=387.1352).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is directly purified through preparative HPLC

Sources & evidence

ORD record
ord-04b00e900b5248d4a5d176e02855e828
Source dataset
uspto-grants-2016_04
Patent number
US09303044B2

Reaction notes

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