Methyl bromoacetate → HCID 69253830, compound

HRID 902709Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of (3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-N-methyl-amine (81 mg, 0.15 mmol) in methanol (15 ml) was treated with bromo-acetic acid methyl ester (46 mg, 0.30 mmol) diisopropylethylamine (46 mg, 0.36 mmol). The resulting solution was heated at 50° C. for 4 hours, cooled down and concentrated. The crude material was dissolved in EtOAc and washed with brine (1×), dried over sodium sulfate, and filtered. The filtrate was concentrated to afford title compound as an oil (70 mg, 76%). MS(ES) m/e 625.2 (M+).

Workup

temperaturecooled down
concentrationconcentrated
dissolutionThe crude material was dissolved in EtOAc
washwashed with brine (1×)
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-885a856e59c04d368545bc0cb0af59d2
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365085B2

Reaction notes

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