(4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine → HCID 67324310, compound

HRID 1397265Notes

Reaction equation

HRID 1397265 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:12]3([CH2:18][NH2:19])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]([C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([C:31]2[N:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[O:33][N:32]=2)[CH:30]=1)[C:25](O)=[O:26])[CH3:21]>>[CH2:20]([C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([C:31]2[N:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[O:33][N:32]=2)[CH:30]=1)[C:25]([NH:19][CH2:18][C:12]1([C:9]2[S:10][CH:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=2)[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)=[O:26])[CH3:21]

Participants

3

Reactant 2

HCID 67322930(4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamineHCID 67325171HCID 67325171, compound

Product 1

HCID 67324310HCID 67324310, compoundYield 45%

Procedure

This compound was synthesized from (4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine and 3-ethyl-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described in example 8 step 6 (85 mg, yield 45%). 1H NMR (400 MHz, CDCl3) δ 8.29 (s, 1H), 8.05 (s, 1H), 7.89 (m, 2H), 7.80 (s, 1H), 7.52 (m, 2H), 7.37-7.29 (m, 3H), 4.00-3.94 (m, 2H), 3.89 (d, J=5.5 Hz, 2H), 3.78-3.72 (ddd, J=11.7 Hz, 7.8 Hz, 3.3 Hz, 2H), 2.69 (q, J=7.7 Hz, 2H), 2.36-2.30 (ddd, J=13.6 Hz, 6.5 Hz, 3.3 Hz, 2H), 2.08-2.02 (ddd, J=13.6 Hz, 7.7 Hz, 3.3 Hz, 2H), 1.23 (t, J=7.7 Hz, 3H). MS (ESI) m/z: Calculated for C27H25F3N4O3S: 542.16. found: 543.2 (M+H)+.

Sources & evidence

ORD record
ord-842c1600401f41758a0e8435f382bee7
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

Loading…