Methylamine → HCID 71532661, compound

HRID 2274534Notes

Reaction equation

[F:1][C:2]([F:38])([F:37])[C@H:3]([OH:36])[CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:26])([F:25])[F:24])[CH:17]=2)[CH2:7][CH:6]1[C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=1)[C:30](O)=[O:31].CCN(C(C)C)C(C)C.[CH3:48][NH2:49].C(N=C=NCCCN(C)C)C>CO>[CH3:48][NH:49][C:30](=[O:31])[C:29]1[CH:33]=[CH:34][CH:35]=[C:27]([CH:6]2[CH2:7][N:8]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:24])([F:25])[F:26])[CH:17]=3)[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:5]2[CH2:4][C@@H:3]([OH:36])[C:2]([F:1])([F:38])[F:37])[CH:28]=1

Participants

Conditions

Temperature: 25 °C

Procedure

3-{1-[(R)-3,3,3-trifluoro-2-hydroxypropyl]-4-[3-(trifluoromethoxy)benzyl]-1,2,3,4-tetrahydroquinoxalin-2-yl}benzoic acid (100 mg, 0.185 mmol) (from Scheme A12) was dissolved in MeOH (925 μl), Hunig's Base (97 μl, 0.555 mmol), methylamine (93 μl, 0.185 mmol), and 3-(ethyliminomethyleneamino)-N,N-dimethyl-propan-1-amine (106 mg, 0.555 mmol) were added, and the mixture was stirred at 25° C. overnight. The product was purified on a reverse phase column, 10-90% MeCN/H2O gradient, 0.1% TFA modifier, yielding Example 19, N-methyl-3-{1-[(R)-3,3,3-trifluoro-2-hydroxypropyl]-4-[3-(trifluoro-methoxy)benzyl]-1,2,3,4-tetrahydro quinoxalin-2-yl}benzamide. MS m/z=554.04.

Workup

customThe product was purified on a reverse phase column, 10-90% MeCN/H2O gradient, 0.1% TFA modifier

Sources & evidence

ORD record: ord-c27a0d634a684767b93fdf2f76c61eee
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126976B2

Reaction notes

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