2-Pyrazinecarboxylic acid → HCID 117702478, compound

HRID 1503268Notes

Reaction equation

HRID 1503268 reaction equation
CC1SC=C([C:7]#[C:8][C@:9]23[CH2:16][C@:13]([NH:17][C:18](C4C=NC=CN=4)=[O:19])([CH2:14][CH2:15]2)[CH2:12][CH2:11][CH2:10]3)N=1.[CH3:26][C:27]1[S:28][CH:29]=[C:30](C#C[C@@]23C[C@@](NC(C4C=NC=CN=4)=O)(CC2)CCC3)[N:31]=1.[N:51]1[CH:56]=[CH:55][N:54]=[CH:53][C:52]=1C(O)=O>>[CH3:26][C:27]1[S:28][CH:29]=[C:30]([C:18]([NH:17][C@@:13]23[CH2:16][C@@:9]([C:8]#[C:7][C:52]4[CH:53]=[N:54][CH:55]=[CH:56][N:51]=4)([CH2:15][CH2:14]2)[CH2:10][CH2:11][CH2:12]3)=[O:19])[N:31]=1

Participants

4

Reactant 3

HCID 10472-Pyrazinecarboxylic acidHCID 117702548HCID 117702548, compoundHCID 117702819HCID 117702819, compound

Product 1

HCID 117702478HCID 117702478, compound

Procedure

Examples 52 and 53 of table 1, N-((1R,5S)-5-((2-methylthiazol-4-yl)ethynyl)bicyclo[3.2.1]octan-1-yl)pyrazine-2-carboxamide and N-((1S,5R)-5-((2-methylthiazol-4-yl)ethynyl)bicyclo[3.2.1]octan-1-yl)pyrazine-2-carboxamide, were prepared analogously to Example 14 from commerically available pyrazine-2-carboxylic acid and intermediate 7-A or 7-B at ˜0.1 mmol reaction scale, respectively. 1H NMR (500 MHz, CDCl3): δ 9.38 (d, J=1.4 Hz, 1H), 8.74 (d, J=2.5 Hz, 1H), 8.50 (m, 1H), 7.90 (s, 1H), 7.18 (s, 1H), 2.69 (s, 3H), 2.49 (m, 1H), 2.29-2.13 (m, 3H), 2.02 (m, 2H), 1.91 (d, J=8.4 Hz, 1H), 1.86-1.71 (m, 5H); ESI-MS m/z: 353 (M+H)+.

Sources & evidence

ORD record
ord-2c4bf205350c4d77a9c78141e98af3ac
Source dataset
uspto-grants-2015_12
Patent number
US09212165B2

Reaction notes

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