Trifluoroacetic acid → HCID 71668135, compound

HRID 624674Notes

Reaction equation

HRID 624674 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:20]2[S:42][C:23]3=[N:24][C:25]([N:29]4[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31][CH2:30]4)=[CH:26][C:27](=[O:28])[N:22]3[N:21]=2)[CH:5]=[C:6]([NH:8][C:9](=[O:19])[CH2:10][NH:11]C(OC(C)(C)C)=O)[CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:11][CH2:10][C:9]([NH:8][C:6]1[CH:5]=[C:4]([C:20]2[S:42][C:23]3=[N:24][C:25]([N:29]4[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]4)=[CH:26][C:27](=[O:28])[N:22]3[N:21]=2)[CH:3]=[C:2]([Br:1])[CH:7]=1)=[O:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89711498HCID 89711498, compound

Product 1

HCID 71668135HCID 71668135, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(2-(3-bromo-5-(2-(tert-butoxycarbonylamino)-acetamido)phenyl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate (30 mg, 0.045 mmol) in DCM (2 ml) is added TFA (0.5 ml) and the mixture is stirred for 1 h. After the removal of DCM in vacuo, the crude residue is directly purified by preparative HPLC to give the desired product, 2-amino-N-(3-bromo-5-(5-oxo-7-(piperazin-1-yl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-2-yl)phenyl)acetamide: 1H NMR (400 MHz, DMSO-d6) δ 8.70-8.20 (br.s., 3H), 8.19 (t, J=1.8 Hz, 1H), 8.11 (t, J=1.8 Hz, 1H), 7.83 (t, J=1.8 Hz, 1H), 5.61 (s, 1H), 3.84 (s, 2H), 3.79 (t, J=5.2 Hz, 4H), 3.18 (t, J=5.2 Hz, 4H); LC/MS: tR=2.743 min; HRMS: m/z (M+H+)=464.0495 and 466.0479 (Calculated for C17H19BrN7O2S=464.0499 and 466.0479).

Workup

  1. customAfter the removal of DCM in vacuo
  2. customthe crude residue is directly purified by preparative HPLC

Sources & evidence

ORD record
ord-3153307ec7e040ff97725736dff6e906
Source dataset
uspto-grants-2016_04
Patent number
US09303044B2

Reaction notes

Loading…