Triethylamine → HCID 68291220, compound

HRID 1527993Notes

Reaction equation

Cl.[F:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[NH:10][C:9]2=[O:19])=[CH:5][C:4]=1[C:22]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:23].[C:30]([O:34][C:35]([N:37]1[CH2:41][CH2:40][CH2:39][C@:38]1([CH3:45])[C:42](O)=[O:43])=[O:36])([CH3:33])([CH3:32])[CH3:31].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>C(#N)C>[O:19]=[C:9]1[NH:10][C:11](=[O:18])[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:8]1[CH2:7][C:6]1[CH:20]=[CH:21][C:3]([F:2])=[C:4]([CH:5]=1)[C:22]([N:24]1[CH2:29][CH2:28][N:27]([C:42]([C@@:38]2([CH3:45])[CH2:39][CH2:40][CH2:41][N:37]2[C:35]([O:34][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:36])=[O:43])[CH2:26][CH2:25]1)=[O:23]

Participants

Conditions

Temperature: 25 °C

Procedure

1-(4-fluoro-3-(piperazine-1-carbonyl)benzyl)quinazoline-2,4(1H,3H)-dione hydrochloric acid (30b, 37 mg) was suspended in acetonitrile (1.5 mL), treated with (R)-1-(tert-butoxycarbonyl)-2-methylpyrrolidine-2-carboxylic acid (40a, 30 mg), HATU (47 mg), and Et3N (0.5 mL) sequentially. The reaction mixture was stirred at ambient temperature (25° C.) for 19 hrs. The reaction mixture was directly purified by flash chromatography with MeOH—CH2Cl2 (0-20% gradient elution) to afford the desired product, (R)-tert-butyl 2-(4-(5-((2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl)methyl)-2-fluorobenzoyl)piperazine-1-carbonyl)-2-methylpyrrolidine-1-carboxylate (40b) as the major fraction (colorless oil, 50 mg). MS (ESI): m/z=594 (M+H+)

Workup

customThe reaction mixture was directly purified by flash chromatography with MeOH—CH2Cl2 (0-20% gradient elution)

Sources & evidence

ORD record: ord-55e1adc903524580aab5f861b0fdc318
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090568B2

Reaction notes

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