Methylamine → 7-(3-Amino-propyl)-9-chloro-2-(3,4-dimethoxy-phenylamino)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one

HRID 2373436Notes

Reaction equation

HRID 2373436 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[N:12]=[C:13]([NH:16][C:17]4[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=4)[N:14]=[CH:15][C:10]=3[CH2:9][C:8](=[O:27])[N:7]([CH2:28][CH2:29][CH2:30][N:31]3C(=O)C4C(=CC=CC=4)C3=O)[C:6]=2[CH:42]=1.CN>C(O)C.ClCCl>[NH2:31][CH2:30][CH2:29][CH2:28][N:7]1[C:8](=[O:27])[CH2:9][C:10]2[CH:15]=[N:14][C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=3)=[N:12][C:11]=2[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:42][C:6]1=2

Participants

5

Reactant 2

HCID 6329MethylamineHCID 598514412-{3-[9-Chloro-2-(3,4-dimethoxy-phenylamino)-6-oxo-5,6-dihydrobenzo[b]pyrimido[4,5-d]azepin-7-yl]-propyl}-isoindole-1,3-dione

Product 1

HCID 598515747-(3-Amino-propyl)-9-chloro-2-(3,4-dimethoxy-phenylamino)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 2-{3-[9-chloro-2-(3,4-dimethoxy-phenylamino)-6-oxo-5,6-dihydrobenzo[b]pyrimido[4,5-d]azepin-7-yl]-propyl}-isoindole-1,3-dione (I-40-c) (51 mg, 0.09 mmol) in ethanol (1.5 mL) was added methylamine (40% by wt in H2O, 0.5 mL). After stirring for 2.5 h at room temperature, the solution was diluted with dichloromethane and washed with water. The organics were dried over magnesium sulfate and concentrated. Preparative HPLC gave I-40: MS Rt═1.32 min. m/z═454 (M+H).

Workup

  1. washwashed with water
  2. dry with materialThe organics were dried over magnesium sulfate
  3. concentrationconcentrated
  4. customPreparative HPLC gave

Sources & evidence

ORD record
ord-49e8728f1ff944a9a33fe583c5ee2ec3
Source dataset
uspto-grants-2008_12
Patent number
US07459448B2

Reaction notes

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