4-Methylmorpholine → HCID 57887275, compound

HRID 1819525Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([NH2:13])[CH2:10][C@H:9]1[C:14](=[O:30])[NH:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]2=[O:28])=[CH:18][C:17]=1[F:29])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:31][C:32]1[S:36][C:35]([C:37](O)=[O:38])=[CH:34][CH:33]=1.CN1CCOCC1>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([NH:13][C:37]([C:35]2[S:36][C:32]([Cl:31])=[CH:33][CH:34]=2)=[O:38])[CH2:10][C@H:9]1[C:14](=[O:30])[NH:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]2=[O:28])=[CH:18][C:17]=1[F:29])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 25 °C

Procedure

(2S,4S)-4-Amino-2-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (90 mg) was dissolved in acetonitrile (0.75 ml). A solution of 5-chlorothiophene-2-carboxylic acid (53 mg), NMM (33 mg) and IBCF (44 mg) in acetonitrile (0.75 ml), which was stirred for 30 min at 25° C., was added to the first solution. The complete mixture was stirred for 72 h at 25° C., evaporated to dryness and purified by chromatography (silica gel; gradient: n-heptane->AcOEt) to yield (2S,4S)-4-[(5-chloro-thiophene-2-carbonyl)-amino]2-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (46 mg) as colorless solid. MH+=561.3 (Cl-isotopes)

Workup

additionwas added to the first solution
customevaporated to dryness
custompurified by chromatography (silica gel; gradient: n-heptane->AcOEt)

Sources & evidence

ORD record: ord-8f83768b8f8d4ba9950997a23307d4db
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601752B2

Reaction notes

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