2486-69-3 → 4-(7,7-difluoro-9-isopropyl-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-benzoic acid

HRID 1676830

Reaction equation

HRID 1676830 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[C:9]([F:15])([F:14])[CH2:8][N:7]([CH:16]([CH3:18])[CH3:17])[C:6]=2[N:19]=1.[NH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][C:22]=1[O:30][CH3:31]>C(O)C.O.Cl>[F:14][C:9]1([F:15])[CH2:8][N:7]([CH:16]([CH3:18])[CH3:17])[C:6]2[N:19]=[C:2]([NH:20][C:21]3[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][C:22]=3[O:30][CH3:31])[N:3]=[CH:4][C:5]=2[N:11]([CH3:12])[C:10]1=[O:13]

Participants

4

Reactant 2

HCID 2880572486-69-3HCID 866359002-Chloro-7,7-difluoro-9-isopropyl-5-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one

Product 1

HCID 445467354-(7,7-difluoro-9-isopropyl-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-benzoic acidYield 55.8%

Reagents, catalysts & solvents 1

HCID 86604601Ethanol water hydrochloric acidSolvent

Procedure

A mixture of 0.5 g (0.0017 mole) of 2-chloro-7,7-difluoro-9-isopropyl-5-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VII-292b) and 0.35 g (0.002 mole) of 4-amino-3-methoxy-benzoic acid in 20 mL of ethanol-water-hydrochloric acid (20:80:1) was refluxed for 18 hours, then cooled and partially concentrated under reduced pressure. The resulting solid was collected by filtration, washed with 0.5M hydrochloric acid and water and dried to give 0.40 g of 4-(7,7-difluoro-9-isopropyl-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-benzoic acid (I-292).

Workup

  1. temperaturewas refluxed for 18 hours
  2. temperaturecooled
  3. concentrationpartially concentrated under reduced pressure
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with 0.5M hydrochloric acid and water
  6. customdried

Sources & evidence

ORD record
ord-de0c618d28ef401b971d2e117d7e0c4e
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Linked notes

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