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

HRID 2234348Notes

Reaction equation

HRID 2234348 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:12]=[CH:13][C:14]3[N:20]([CH3:21])[CH2:19][CH2:18][CH2:17][N:16]([CH:22]4[CH2:26][CH2:25][CH2:24][CH2:23]4)[C:15]=3[N:27]=2)=[C:6]([O:28][CH3:29])[CH:5]=1.Cl>O.CO.C(Cl)Cl>[CH:22]1([N:16]2[CH2:17][CH2:18][CH2:19][N:20]([CH3:21])[C:14]3[CH:13]=[N:12][C:11]([NH:10][C:7]4[CH:8]=[CH:9][C:4]([C:3]([OH:30])=[O:2])=[CH:5][C:6]=4[O:28][CH3:29])=[N:27][C:15]2=3)[CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68683926Methyl4-[(9-cyclopentyl-5-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzoate2×

Product 1

HCID 686847994-[(9-Cyclopentyl-5-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzoic acidYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Methyl4-[(9-cyclopentyl-5-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-3-methoxybenzoate (Intermediate 7; 250 mg, 0.61 mmol) and HCl (2 mL, concentrated aqueous) were suspended in water (4 mL) and heated at reflux for 24 h. The reaction mixture was then cooled to ambient temperature and the volatiles were removed under reduced pressure. The solid obtained was dissolved in MeOH:DCM (1:10, 40 mL) and washed with NaHCO3 (saturated aqueous, 40 mL). The organic layer was then dried (MgSO4), filtered and the volatiles removed under reduced pressure to afford the title compound (240 mg, 99%) as a solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 h
  3. customthe volatiles were removed under reduced pressure
  4. customThe solid obtained
  5. washwashed with NaHCO3 (saturated aqueous, 40 mL)
  6. dry with materialThe organic layer was then dried (MgSO4)
  7. filtrationfiltered
  8. customthe volatiles removed under reduced pressure

Sources & evidence

ORD record
ord-e55ac824bdc04332a851f7d3466814ba
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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