Hydrochloric Acid → Methyl4-[(9-cyclopentyl-5-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzoate

HRID 2234349Notes

Reaction equation

HRID 2234349 reaction equation
S(C)C.[CH3:4][O:5][C:6](=[O:34])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[N:15]=[CH:16][C:17]3[N:23]([CH3:24])[C:22](=O)[CH2:21][CH2:20][N:19]([CH:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)[C:18]=3[N:31]=2)=[C:9]([O:32][CH3:33])[CH:8]=1.Cl>C1COCC1.O>[CH3:4][O:5][C:6](=[O:34])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[N:15]=[CH:16][C:17]3[N:23]([CH3:24])[CH2:22][CH2:21][CH2:20][N:19]([CH:26]4[CH2:27][CH2:28][CH2:29][CH2:30]4)[C:18]=3[N:31]=2)=[C:9]([O:32][CH3:33])[CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 1068Dimethyl SulfideHCID 68682079methyl4-[(9-cyclopentyl-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzoate2×

Product 1

HCID 68683926Methyl4-[(9-cyclopentyl-5-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzoateYield 89.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

BH3.SMe2 (1.36 mL, 5.0 M in Et2O, 6.8 mmol) was added to solution of methyl4-[(9-cyclopentyl-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzoate (Intermediate 8; 290 mg, 0.68 mmol) in THF (4 mL) and stirred for 5 h at ambient temperature under an atmosphere of nitrogen. HCl (10 mL, concentrated aqueous) was added and the resulting solution was stirred at ambient temperature for 16 h. The HCl solution was then diluted with water (50 mL), and loaded onto an SCX-2 column. The SCX-2 column was then washed with water (50 mL) and MeOH (50 mL). The product was then eluted from the SCX-2 column with NH3 (50 mL, 7M in MeOH). The volatiles were then removed under reduced pressure to afford the title compound (250 mg, 89%) as a solid.

Workup

  1. additionwas added
  2. stirringthe resulting solution was stirred at ambient temperature for 16 h
  3. washThe SCX-2 column was then washed with water (50 mL) and MeOH (50 mL)
  4. washThe product was then eluted from the SCX-2 column with NH3 (50 mL, 7M in MeOH)
  5. customThe volatiles were then removed under reduced pressure

Sources & evidence

ORD record
ord-a7452678a57446adb483e5d85d49ac85
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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