(2-(Methylthio)ethyl)amine → HCID 86654751, compound

HRID 1916436Notes

Reaction equation

HRID 1916436 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([C:13]2([C:30]([F:33])([F:32])[F:31])[O:17][N:16]=[C:15]([C:18]3[N:23]4[CH:24]=[CH:25][N:26]=[C:22]4[C:21]([C:27](O)=[O:28])=[CH:20][CH:19]=3)[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:36][S:37][CH2:38][CH2:39][NH2:40]>>[CH3:36][S:37][CH2:38][CH2:39][NH:40][C:27]([C:21]1[C:22]2[N:23]([CH:24]=[CH:25][N:26]=2)[C:18]([C:15]2[CH2:14][C:13]([C:5]3[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=[C:3]([C:2]([F:35])([F:1])[F:34])[CH:4]=3)([C:30]([F:32])([F:33])[F:31])[O:17][N:16]=2)=[CH:19][CH:20]=1)=[O:28]

Participants

3

Reactant 2

HCID 87697(2-(Methylthio)ethyl)amineHCID 86654752HCID 86654752, compound

Product 1

HCID 86654751HCID 86654751, compound

Procedure

Using a procedure similar to that described in Example 1, except using 5-[5-(3,5-bistrifluoromethylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-imidazo[1,2-a]pyridine-8-carboxylic acid (45 mg) and 2-methylthioethylamine (0.016 mL), the title compound was isolated as an orange-reddish solid (11.9 mg, 23%). MS (ES): M/Z [M+H]=585. 1H NMR (400 MHz, CHLOROFORM-d): 2.22 (s, 3H), 2.85 (t, J=6.8 Hz, 2H), 3.82 (q, J=6.6 Hz, 2H), 4.01 (d, J=17.0 Hz, 1H), 4.44 (d, J=16.8 Hz, 1H), 7.21 (d, J=7.6 Hz, 1H), 7.85 (s, 1H), 8.02 (s, 1H), 8.12 (s, 2H), 8.28 (d, J=7.6 Hz, 1H), 8.90 (d, J=1.0 Hz, 1H), 10.67 (br. s., 1H). 19F NMR (376 MHz, CHLOROFORM-d): −80.0 (s, 3F), −63.3 (s, 6F).

Sources & evidence

ORD record
ord-0d44d95493ab423db6be08138ff81b15
Source dataset
uspto-grants-2013_12
Patent number
US08618126B2

Reaction notes

Loading…