Hydrochloric Acid → [2-(3-cyclopropyl-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester

HRID 896346Notes

Reaction equation

HRID 896346 reaction equation
[CH:1]1([N:4]2[C:13](=[O:14])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]2=[O:15])[CH2:3][CH2:2]1.CC(N=P(N1CCCC1)(N1CCCC1)N1CCCC1)(C)C.[C:37]([O:41][C:42](=[O:61])[NH:43][CH2:44][C:45]1[CH:60]=[CH:59][C:48]2[N:49]([CH2:54][CH2:55][CH:56]([CH3:58])[CH3:57])[C:50]([CH2:52]Cl)=[N:51][C:47]=2[CH:46]=1)([CH3:40])([CH3:39])[CH3:38].Cl>CN(C=O)C>[C:37]([O:41][C:42](=[O:61])[NH:43][CH2:44][C:45]1[CH:60]=[CH:59][C:48]2[N:49]([CH2:54][CH2:55][CH:56]([CH3:57])[CH3:58])[C:50]([CH2:52][N:6]3[C:7]4[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:13](=[O:14])[N:4]([CH:1]4[CH2:3][CH2:2]4)[C:5]3=[O:15])=[N:51][C:47]=2[CH:46]=1)([CH3:38])([CH3:40])[CH3:39]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3856267tert-Butylimino-tri(pyrrolidino)phosphoraneHCID 172214493-cyclopropyl-1H-quinazoline-2,4-dioneHCID 59561810HCID 59561810, compound

Product 1

HCID 69718855[2-(3-cyclopropyl-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl esterYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the 3-cyclopropyl-1H-quinazoline-2,4-dione (148 mg, 0.73 mmol) in DMF (10 mL) was added BTPP (684 mg, 2.19 mmol). After stirring for 20 minutes, [2-chloromethyl-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester; HCl salt (294 mg, 0.73 mmol) was added and the resulting mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue precipitated from water. The title compound was collected by filtration and extensively washed with water and dried in vacuo to yield [2-(3-cyclopropyl-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester as an off-white solid (310 mg, 80%):

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customThe solvent was removed in vacuo
  3. customthe residue precipitated from water
  4. filtrationThe title compound was collected by filtration
  5. washextensively washed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-416c61d600ae4d5dafd6bb752c73ab04
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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