Dichloromethane → 6-{4-[(3-Amino-propylamino)-methyl]-phenyl}-1H-imidazo[1,2-a]pyrimidin-7-one hydrochloride salt

HRID 717739Notes

Reaction equation

HRID 717739 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][N:11](C(OC(C)(C)C)=O)[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:20](=[O:28])[N:21]=[C:22]3[NH:27][CH:26]=[CH:25][N:23]3[CH:24]=2)=[CH:15][CH:14]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)[Cl:45]>>[ClH:45].[NH2:7][CH2:8][CH2:9][CH2:10][NH:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[C:20](=[O:28])[N:21]=[C:22]3[NH:27][CH:26]=[CH:25][N:23]3[CH:24]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 178453510HCID 178453510, compound

Product 1

HCID 1784792196-{4-[(3-Amino-propylamino)-methyl]-phenyl}-1H-imidazo[1,2-a]pyrimidin-7-one hydrochloride saltYield 100%

Procedure

{(3-{tert-Butoxycarbonyl-[4-(7-oxo-1,7-dihydro-imidazo[1,2-a]pyrimidin-6-yl)-benzyl]-amino}-propyl)-carbamic acid tert-butyl ester (48 mg, 0.097 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 (35 mg, 100%). 1NMR (300 MHz, CD3OD): δ 8.90 (s, 1H), 7.79 (s, 1H), 7.77 (d, J=8.2 Hz, 2H), 7.70 (d, J=8.2 Hz, 2H), 7.67 (s, 1H), 4.33 (s, 2H), 3.23 (t, J=8.1 Hz, 2H), 3.06 (t, J=7.5 Hz, 2H), 2.15 (m, 2H). LCMS (EI) m/z: 297.1 (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-0e3e8166b04148c2977fb05307e67c73
Source dataset
uspto-grants-2015_11
Patent number
US09193731B2

Reaction notes

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