Isopropanol → 2-[5-Chloro-2-(7-oxo-6,7,8,9-tetrahydro-5H-benzocyclo-hepten-2-ylamino)-pyrimidin-4-ylamino]-N-methyl-benzamide

HRID 1687003Notes

Reaction equation

HRID 1687003 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([NH:13][CH3:14])=[O:12])[C:5]([Cl:19])=[CH:4][N:3]=1.[NH2:20][C:21]1[CH:22]=[CH:23][C:24]2[CH2:30][CH2:29][C:28](=[O:31])[CH2:27][CH2:26][C:25]=2[CH:32]=1.C(O)(C)C>Cl>[Cl:19][C:5]1[C:6]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([NH:13][CH3:14])=[O:12])=[N:7][C:2]([NH:20][C:21]2[CH:22]=[CH:23][C:24]3[CH2:30][CH2:29][C:28](=[O:31])[CH2:27][CH2:26][C:25]=3[CH:32]=2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 450982242-Amino-8,9-dihydro-5H-benzo[7]annulen-7(6H)-oneHCID 579741322-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamide

Product 1

HCID 251573272-[5-Chloro-2-(7-oxo-6,7,8,9-tetrahydro-5H-benzocyclo-hepten-2-ylamino)-pyrimidin-4-ylamino]-N-methyl-benzamideYield 50%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

Into a microwave vial was placed 2-(2,5-dichloro-pyrimidin-4-ylamino)-N-methyl-benzamide (50 mg, 0.0002 mol) and 2-amino-5,6,8,9-tetrahydro-benzocyclohepten-7-one (38 mg, 0.00022 mol) in isopropyl alcohol (5 mL, 0.06 mol) with 4 M HCl (3 drops). The mixture was subjected microwaves at 130° C. for 10 minutes. Trace starting materials were present so the reaction mixture was resubjected to the same microwave conditions. The resulting solid was collected by filtration and washed with cold methylene chloride and dried in a vacuum oven at 50° C. overnight to give 38 mg (50%) of an off-white solid 2-[5-Chloro-2-(7-oxo-6,7,8,9-tetrahydro-5H-benzocyclo-hepten-2-ylamino)-pyrimidin-4-ylamino]-N-methyl-benzamide. MP: 262-269° C.; 1HNMR (400 MHz, DMSO-d6) δ 11.63 (s, 1H), 9.50 (s, 1H), 8.78 (d, 1H, J=5.3 Hz), 8.69 (d, 1H, J=8.08 Hz), 8.24 (s, 1H), 7.76 (d, 1H, J=7.58), 7.59 (s, 1H), 7.48 (t, 1H, J=7.58 Hz), 7.42 (d, 1H, J=7.58), 7.17 (t, 1H, J=8 Hz), 2.77-2.85 (m, 8H), 2.5 (d, 3H); MS (m/e) 436 (M+1).

Workup

  1. customat 130° C.
  2. customfor 10 minutes
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with cold methylene chloride
  5. customdried in a vacuum oven at 50° C. overnight

Sources & evidence

ORD record
ord-af5bb5f9a882452a8f2951c9f2df5551
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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