1,1'-Carbonyldiimidazole → HCID 68388823, compound

HRID 927289Notes

Reaction equation

HRID 927289 reaction equation
[NH2:1][C:2]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([NH:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].C1N=CN([C:21](N2C=NC=C2)=[O:22])C=1>C1COCC1>[C:7]([N:6]1[C:4](=[O:5])[C:3]2[C:2](=[C:14]([CH3:15])[CH:13]=[CH:12][CH:11]=2)[NH:1][C:21]1=[O:22])([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 16774928HCID 16774928, compound

Product 1

HCID 68388823HCID 68388823, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compounds of this invention can be prepared as illustrated by the exemplary reaction in Scheme 3. Reaction of 2-amino-3-methylbenzoic acid with triphosgene in THF produced 8-methyl-1H-benzo[d][1,3]oxazine-2,4-dione, which was treated with tert-butylamine and DMAP in DMF to produce 2-amino-N-tert-butyl-3-methylbenzamide. Reaction of the benzamide with CDI in THF produced 3-tert-butyl-8-methylquinazoline-2,4(1H,3H)-dione, which was reacted with methyl 3-(bromomethyl)benzoate and MeONa in DMF, followed by treatment with hydrochloric acid aqueous solution, to produce 8-methyl-1-(3-carboxybenzyl)quinazoline-2,4(1H,3H)-dione. Coupling of the acid with 2-(piperazin-1-yl)pyrimidine in the presence of coupling agents, such as HATU and DIPEA in DMF, produced the targeted compound 8-methyl-1-(3-(4-(pyrimidin-2-yl)piperazine-1-carbonyl)benzyl)quinazoline-2,4(1H,3H)-dione.

Sources & evidence

ORD record
ord-e0862ba6ad8a4605a4c598b6e7a28620
Source dataset
uspto-grants-2016_03
Patent number
US09290460B2

Reaction notes

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