(2-(Methylthio)ethyl)amine → HCID 53252790, compound

HRID 2207317Notes

Reaction equation

HRID 2207317 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:26]([F:29])([F:28])[F:27])[O:13][N:12]=[C:11]([C:14]3[N:15]4[C:19]([C:20]([C:23]([OH:25])=O)=[CH:21][CH:22]=3)=[CH:18][CH:17]=[CH:16]4)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:30][S:31][CH2:32][CH2:33][NH2:34]>>[CH3:30][S:31][CH2:32][CH2:33][NH:34][C:23]([C:20]1[C:19]2[N:15]([CH:16]=[CH:17][CH:18]=2)[C:14]([C:11]2[CH2:10][C:9]([C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=3)([C:26]([F:27])([F:28])[F:29])[O:13][N:12]=2)=[CH:22][CH:21]=1)=[O:25]

Participants

3

Reactant 2

HCID 87697(2-(Methylthio)ethyl)amineHCID 67247370HCID 67247370, compound

Product 1

HCID 53252790HCID 53252790, compound

Procedure

Using a procedure similar to that described in Example 1, except using 5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-indolizine-8-carboxylic acid (37 mg, described above in Example 3) and 2-methylthioethylamine, the title compound was isolated as an orange-reddish solid (21.2 mg, 49%). MS (ES): M/Z [M+H]=516. 1H NMR (400 MHz, CHLOROFORM-d): 2.17 (s, 3H), 2.83 (t, J=6.2 Hz, 2H), 3.75 (q, J=6.0 Hz, 2H), 3.91 (d, J=16.6 Hz, 1H), 4.28 (d, J=16.6 Hz, 1H), 6.83 (d, J=7.4 Hz, 1H), 7.02-7.08 (m, 1H), 7.17 (d, J=7.2 Hz, 1H), 7.46 (t, J=1.7 Hz, 1H), 7.55 (s, 2H), 8.73 (d, J=1.6 Hz, 1H). 19F NMR (376 MHz, CHLOROFORM-d): −79.8 (s, 3F).

Sources & evidence

ORD record
ord-43f35a4e996c45068002cee866fe2ed5
Source dataset
uspto-grants-2016_06
Patent number
US09376434B2

Reaction notes

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