HCID 19417527, compound → HCID 69950069, compound

HRID 1397271Notes

Reaction equation

HRID 1397271 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.[C:20]([CH:22]1[CH2:24][CH:23]1[C:25](O)=[O:26])#[N:21]>>[C:20]([CH:22]1[CH2:24][CH:23]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])#[N:21]

Participants

3

Reactant 2

HCID 19417527HCID 19417527, compoundHCID 67322930(4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine

Product 1

HCID 69950069HCID 69950069, compoundYield 29%

Procedure

This compound was synthesized from (4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine and 2-cyanocyclopropanecarboxylic acid as described in example 8 step 6 (90 mg, yield 29%): 1H NMR (400 MHz, CDCl3) δ 7.92 (m, 2H), 7.52-7.46 (m, 3H), 7.41-7.37 (m, 1H), 6.72 (t, J=5.3 Hz, 1H), 3.92-3.86 (m, 2H), 3.75-3.68 (m, 4H), 2.30-2.22 (dddd, J=13.2 Hz, 9.8 Hz, 6.5 Hz, 3.4 Hz, 2H), 1.99-1.89 (m, 4H), 1.52-1.47 (ddd, J=9.1 Hz, 5.8 Hz, 4.6 Hz, 1H), 1.38-1.33 (ddd, J=8.6 Hz, 6.1 Hz, 4.9 Hz, 1H). MS (ESI) m/z: Calculated for C20H21N3O2S: 367.14. found: 368.2 (M+H)+.

Sources & evidence

ORD record
ord-35c091934f91471ca46fec4bf8b20039
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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