tert-Butylimino-tri(pyrrolidino)phosphorane → HCID 20814122, compound

HRID 896378Notes

Reaction equation

[F:1][C:2]([F:17])([F:16])[CH2:3][N:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]1=[O:15].CC(N=P(N1CCCC1)(N1CCCC1)N1CCCC1)(C)C.[C:39]([O:43][C:44](=[O:65])[NH:45][CH2:46][C:47]1[CH:64]=[CH:63][C:50]2[N:51]([CH2:56][CH2:57][CH2:58][S:59]([CH3:62])(=[O:61])=[O:60])[C:52]([CH2:54]Cl)=[N:53][C:49]=2[CH:48]=1)([CH3:42])([CH3:41])[CH3:40]>C1COCC1>[C:39]([O:43][C:44](=[O:65])[NH:45][CH2:46][C:47]1[CH:64]=[CH:63][C:50]2[N:51]([CH2:56][CH2:57][CH2:58][S:59]([CH3:62])(=[O:60])=[O:61])[C:52]([CH2:54][N:6]3[C:7]4[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:13](=[O:14])[N:4]([CH2:3][C:2]([F:1])([F:16])[F:17])[C:5]3=[O:15])=[N:53][C:49]=2[CH:48]=1)([CH3:42])([CH3:40])[CH3:41]

Participants

Conditions

Temperature: 23 °C

Procedure

A slurry of 3-(2,2,2-trifluoro-ethyl)-1H-quinazoline-2,4-dione (88 mg, 0.36 mmol) in THF (20 ml) was treated with BTPP (0.33 ml, 1.08 mmol) and stirred for 15 min at 23° C. [2-Chloromethyl-1-(3-methanesulfonyl-propyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester (150 mg, 0.36 mmol) was added and the mixture stirred at 23° C. for 12 h. The solvent was removed and the residue triturated with water. The residue was chromatographed to give 40 mg (18%) of [2-[2,4-dioxo-3-(2,2,2-trifluoro-ethyl)-3,4-dihydro-2H-quinazolin-1-ylmethyl]-1-(3-methanesulfonyl-propyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester as a white solid.

Workup

additionwas added
customThe solvent was removed
customthe residue triturated with water
customThe residue was chromatographed

Sources & evidence

ORD record: ord-3e79d848306f45b786ab1a5c203d2e24
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06919331B2

Reaction notes

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