p-Toluenesulfonic acid monohydrate → HCID 57635023, compound

HRID 2111320Notes

Reaction equation

HRID 2111320 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH:9]([CH3:14])[CH2:8][N:7]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[C:6]=2[N:21]=1.[N:22]1[CH:27]=[CH:26][C:25]([C:28]2[O:29][C:30]3[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][C:31]=3[N:32]=2)=[CH:24][CH:23]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(O)C>[CH:15]1([N:7]2[CH2:8][CH:9]([CH3:14])[C:10](=[O:13])[N:11]([CH3:12])[C:5]3[CH:4]=[N:3][C:2]([NH:37][C:34]4[CH:35]=[CH:36][C:30]5[O:29][C:28]([C:25]6[CH:24]=[CH:23][N:22]=[CH:27][CH:26]=6)=[N:32][C:31]=5[CH:33]=4)=[N:21][C:6]2=3)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 7360092-Pyridin-4-yl-benzooxazol-5-ylamineHCID 87555255HCID 87555255, compound

Product 1

HCID 57635023HCID 57635023, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 0.05 g (0.00016 mole) of (rac)-2-chloro-9-cyclohexyl-5,7-dimethyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VII-19), 0.034 g, 0.00016 mole) of 2-pyridin-4-yl-benzooxazol-5-ylamine, 0.047 g, (0.00024 mole) of p-toluenesulfonic acid monohydrate and 4 mL of 2-propanol was heated at 180 degree for 2 hours in a microwave reactor. The reaction mixture was concentrated. The residue was diluted with dichloromethane and washed twice with saturated sodium bicarbonate solution. The aqueous phase was extracted with dichloromethane. The combined organic phases were washed with brine, dried anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with dichloromethane-methanol (100:0-95:5) to give 0.047 g of (rac)-9-cyclohexyl-5,7-dimethyl-2-(2-pyridin-4-yl-benzooxazol-5-ylamino)-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diaze-pin-6-one (I-26). HRMS (ES+) m/z Calcd for C27H29N7O2+H [(M+H)+]: 484.2456. Found: 484.2456.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionThe residue was diluted with dichloromethane
  3. washwashed twice with saturated sodium bicarbonate solution
  4. extractionThe aqueous phase was extracted with dichloromethane
  5. washThe combined organic phases were washed with brine, dried anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with dichloromethane-methanol (100:0-95:5)

Sources & evidence

ORD record
ord-37bd3208e8b14f50a7d77f1033927139
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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