2-((1S,2S,5S)-6,6-Dimethylbicyclo[3.1.1]heptan-2-yl)acetic acid → N-(3-tert-butylpyrazolo[1,5-a]pyrimidin-2-yl)-2-[(1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]acetamide

HRID 1912969Notes

Reaction equation

HRID 1912969 reaction equation
[C:1]([C:5]1[C:6]([NH2:14])=[N:7][N:8]2[CH:13]=[CH:12][CH:11]=[N:10][C:9]=12)([CH3:4])([CH3:3])[CH3:2].[CH3:15][C:16]1([CH3:27])[C@H:21]2[CH2:22][C@@H:17]1[CH2:18][CH2:19][C@H:20]2[CH2:23][C:24](O)=[O:25]>>[C:1]([C:5]1[C:6]([NH:14][C:24](=[O:25])[CH2:23][C@@H:20]2[CH2:19][CH2:18][C@H:17]3[CH2:22][C@@H:21]2[C:16]3([CH3:15])[CH3:27])=[N:7][N:8]2[CH:13]=[CH:12][CH:11]=[N:10][C:9]=12)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 671611162-((1S,2S,5S)-6,6-Dimethylbicyclo[3.1.1]heptan-2-yl)acetic acidHCID 687554713-Tert-butylpyrazolo[1,5-a]pyrimidin-2-amine

Product 1

HCID 68752775N-(3-tert-butylpyrazolo[1,5-a]pyrimidin-2-yl)-2-[(1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]acetamide

Procedure

The product from Example 105B and the product from Example 4B were processed using the method analogous to that described in Example 137 to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.65-9.70 (bs, 1H), 8.92 (dd, J=6.3, 1.8 Hz, 1H), 8.48 (dd, J=4.1, 1.8 Hz, 1H), 6.99 (dd, J=6.7, 3.9 Hz, 1H), 2.52-2.59 (m, 1H), 2.25-2.47 (m, 3H), 1.78-2.00 (m, 5H), 1.48-1.52 (m, 1H), 1.45 (s, 9H), 1.15-1.21 (bs, 3H), 1.02-1.11 (bs, 3H), 0.91 (d, J=9.3 Hz, 1H); MS (DCI) m/z 355 (M+H)+.

Sources & evidence

ORD record
ord-e85957fc3b6f44fea718d893363f94c6
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

Loading…