tert-Butyl 7-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate → tert-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

HRID 2370617Notes

Reaction equation

HRID 2370617 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[N:12][C:13](S(C)=O)=[N:14][CH:15]=2)[N:10]2[CH:22]=[CH:23][N:24]=[C:9]12.[NH2:25][C:26]1[CH:35]=[C:34]2[C:29]([CH2:30][CH2:31][N:32]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:33]2)=[CH:28][CH:27]=1>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[CH:15]=[N:14][C:13]([NH:25][C:26]3[CH:35]=[C:34]4[C:29]([CH2:30][CH2:31][N:32]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:33]4)=[CH:28][CH:27]=3)=[N:12][C:11]=2[N:10]2[CH:22]=[CH:23][N:24]=[C:9]12

Participants

4

Reactant 2

HCID 22061016tert-Butyl 7-amino-3,4-dihydroisoquinoline-2(1H)-carboxylateHCID 681947574-(2-Chloro-phenyl)-8-methanesulfinyl-4H-3,4,7,9,9b-pentaaza-cyclopenta[a]naphthalen-5-one

Product 1

HCID 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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 1E (0.900 g, 2.501 mmol) and tert-butyl 7-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate (0.994 g, 4.00 mmol) was heated in a capped vial at 90° C. for 1 hour. The reaction mixture were suspended and stirred in ethyl acetate. The solids were filtered and washed with ethyl acetate. The filter cake was stirred in saturated aqueous NaHCO3, filtered, washed with water, and oven-dried to provide the title compound. The filtrate was diluted with ethyl acetate and washed with saturated NaHCO3. The organic layer was dried over MgSO4, filtered, concentrated, and purified on an 80 g column using the ISCO Companion flash system eluting with CH2Cl2/ethyl acetate (6:4 to 5:5) to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.44 (s, 9H), 2.77 (t, J=5.75 Hz, 2H), 3.58 (t, J=5.75 Hz, 2H), 4.54 (s, 2H), 7.07 (d, J=1.59 Hz, 1H), 7.21 (d, J=8.72 Hz, 1H), 7.53-7.66 (m, 5H), 7.69-7.74 (m, 1H), 7.76 (d, J=1.59 Hz, 1H), 9.12 (s, 1H), 10.71 (s, 1H). MS (ESI+) m/z 544.1 (M+H)+.

Workup

  1. filtrationThe solids were filtered
  2. washwashed with ethyl acetate
  3. filtrationfiltered
  4. washwashed with water
  5. customoven-dried

Sources & evidence

ORD record
ord-31abb86f72e141bba48911ae3954ac03
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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