Dichloromethane → HCID 178479218, compound

HRID 717741Notes

Reaction equation

HRID 717741 reaction equation
C(OC(=O)[N:7]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[C:27](=[O:42])[N:28]=[C:29]3[NH:34][C:33]([C:35]4[CH:40]=[CH:39][C:38]([Br:41])=[CH:37][CH:36]=4)=[CH:32][N:30]3[CH:31]=2)=[CH:22][CH:21]=1)[CH2:8][CH2:9][CH2:10][NH:11]C(OC(C)(C)C)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)[Cl:52]>>[ClH:52].[NH2:11][CH2:10][CH2:9][CH2:8][NH:7][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[C:27](=[O:42])[N:28]=[C:29]3[NH:34][C:33]([C:35]4[CH:36]=[CH:37][C:38]([Br:41])=[CH:39][CH:40]=4)=[CH:32][N:30]3[CH:31]=2)=[CH:24][CH:25]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 178453509HCID 178453509, compound

Product 1

HCID 178479218HCID 178479218, compoundYield 100%

Procedure

{4-[2-(4-Bromo-phenyl)-7-oxo-1,7-dihydro-imidazo[1,2-a]pyrimidin-6-yl]-benzyl}-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl ester (100 mg, 0.153 mmol) was dissolved in CH2Cl2 (5 mL), TFA (1 mL) was added and stirred at room temperature for 2 h. The reaction mixture was concentrated and 3 mL of 0.6 N HCl and 2 mL of acetonitrile were added and stirred for 0.5 h, concentrated to a ca. 3 mL and lyophilized to give the title compound (80 mg, 100%). 1NMR (300 MHz, CD3OD): δ 8.99 (s, 1H), 8.24 (s, 1H), 7.75 (m, 8H), 4.30 (s, 2H), 3.32 (t, J=8.1 Hz, 2H), 3.09 (t, J=7.5 Hz, 2H), 2.17 (m, 2H). LCMS (EI) m/z: 454 (M+H+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition3 mL of 0.6 N HCl and 2 mL of acetonitrile were added
  3. stirringstirred for 0.5 h
  4. concentrationconcentrated to a ca. 3 mL

Sources & evidence

ORD record
ord-ac928375cc044a6fab05f26ff922d058
Source dataset
uspto-grants-2015_11
Patent number
US09193731B2

Reaction notes

Loading…