Hydrochloric Acid → HCID 57635042, compound

HRID 2111318Notes

Reaction equation

HRID 2111318 reaction equation
[CH:1]1([N:5]2[CH2:11][CH2:10][C:9](=[O:12])[N:8]([CH3:13])[C:7]3[CH:14]=[N:15][C:16]([NH:18][C:19]4[CH:34]=[CH:33][C:22](C(NC5CCN(C)CC5)=O)=[CH:21][C:20]=4[O:35][CH3:36])=[N:17][C:6]2=3)[CH2:4][CH2:3][CH2:2]1.Cl>O.CO.C(#N)C>[CH:1]1([N:5]2[CH2:11][CH2:10][C:9](=[O:12])[N:8]([CH3:13])[C:7]3[CH:14]=[N:15][C:16]([NH:18][C:19]4[CH:34]=[CH:33][CH:22]=[CH:21][C:20]=4[O:35][CH3:36])=[N:17][C:6]2=3)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 42610361HCID 42610361, compound

Product 1

HCID 57635042HCID 57635042, compoundYield 12.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.23 g (0.00085 mole) of 4-(9-cyclobutyl-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-N-(1-methyl-piperidin-4-yl)-benzamide (I-24) and 3 mL of 1M hydrochloric acid was heated at 180 degree for 45 minutes in a microwave reactor. The cooled mixture was diluted with 2 mL of water, 3 mL of methanol and 2 mL of acetonitrile and then stirred for 15 minutes. The solids were removed by filtration and the aqueous solution was made basic (pH>10). The solid which formed was collected, washed with water, and then purified by C18 reverse phase silica gel chromatography, eluting with an acetonitrile-water gradient (10:90-100:0) to give 0.037 g of 9-cyclobutyl-2-(2-methoxy-phenylamino)-5-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (I-25)

Workup

  1. temperaturewas heated at 180 degree for 45 minutes in a microwave reactor
  2. customThe solids were removed by filtration
  3. customThe solid which formed
  4. customwas collected
  5. washwashed with water
  6. custompurified by C18 reverse phase silica gel chromatography
  7. washeluting with an acetonitrile-water gradient (10:90-100:0)

Sources & evidence

ORD record
ord-545fdb290b5848bcb82526e9392d0be3
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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