Trifluoroacetic acid → Trifluoroacetic acid

HRID 2370618Notes

Reaction equation

HRID 2370618 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:13](=[O:14])[C:12]2[CH:15]=[N:16][C:17]([NH:19][C:20]3[CH:29]=[C:28]4[C:23]([CH2:24][CH2:25][N:26](C(OC(C)(C)C)=O)[CH2:27]4)=[CH:22][CH:21]=3)=[N:18][C:11]=2[N:10]2[CH:37]=[CH:38][N:39]=[C:9]12.[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:13](=[O:14])[C:12]2[CH:15]=[N:16][C:17]([NH:19][C:20]3[CH:29]=[C:28]4[C:23]([CH2:24][CH2:25][NH:26][CH2:27]4)=[CH:22][CH:21]=3)=[N:18][C:11]=2[N:10]2[CH:37]=[CH:38][N:39]=[C:9]12.[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 60168685tert-butyl 7-{[6-(2-chlorophenyl)-5-oxo-5,6-dihydroimidazo[1,2-a]pyrimido[5,4-e]pyrimidin-2-yl]amino}-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 2

HCID 6422Trifluoroacetic acidHCID 681953946-(2-chlorophenyl)-2-(1,2,3,4-tetrahydroisoquinolin-7-ylamino)imidazo[1,2-a]pyrimido[5,4-e]pyrimidin-5(6H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of Example 20 (0.357 g, 0.656 mmol) and trifluoroacetic acid (0.506 mL, 6.56 mmol) in CH2Cl2 (6 mL) was stirred at room temperature for 6 hours. The reaction mixture was concentrated and purified by HPLC as described in Example 1F to provide the title compound as a trifluoroacetic acid salt. 1H NMR (300 MHz, CD3OD) δ ppm 3.14 (t, J=6.35 Hz, 2H), 3.54 (t, J=6.35 Hz, 2H), 4.43 (s, 2H), 7.07 (d, J=1.98 Hz, 1H), 7.31 (d, J=8.33 Hz, 1H), 7.52-7.63 (m, 3H), 7.66-7.72 (m, 2H), 7.76 (s, 1H), 7.87 (d, J=1.98 Hz, 1H), 9.18 (s, 1H). MS (ESI+) m/z 444.2 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-f89782d771a84bb4b835b70445b73406
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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