1-Adamantaneacetyl chloride → 2-(adamantan-1-yl)-N-(3-tert-butylpyrazolo[1,5-a]pyrimidin-2-yl)acetamide

HRID 1912911Notes

Reaction equation

HRID 1912911 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].[C:15]12([CH2:25][C:26](Cl)=[O:27])[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH2:16]1)[CH2:22]2>>[C:15]12([CH2:25][C:26]([NH:14][C:6]3[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[C:9]4[N:10]=[CH:11][CH:12]=[CH:13][N:8]4[N:7]=3)=[O:27])[CH2:22][CH:21]3[CH2:20][CH:19]([CH2:18][CH:17]([CH2:23]3)[CH2:16]1)[CH2:24]2

Participants

3

Reactant 2

HCID 27718821-Adamantaneacetyl chlorideHCID 687554713-Tert-butylpyrazolo[1,5-a]pyrimidin-2-amine

Product 1

HCID 687481532-(adamantan-1-yl)-N-(3-tert-butylpyrazolo[1,5-a]pyrimidin-2-yl)acetamide

Procedure

The product from Example 105B and 1-adamantylacetyl chloride were processed using the method analogous to that described in Example 105C to afford the title compound. 1H NMR (300 MHz, DMSO-d6): δ ppm 1.45 (s, 9H), 1.59-1.67 (m, 12H), 1.95 (br s, 3H), 2.06 (s, 2H), 6.98 (dd, J=6.8, 4.1 Hz, 1H), 8.47 (dd, J=4.1, 1.7 Hz, 1H), 8.95 (dd, J=7.0, 1.9 Hz, 1H), 9.56 (s, 1H); MS (DCI) m/z 367 (M+H)+.

Sources & evidence

ORD record
ord-9328dda5ca264045b83ee4a4f189ba4e
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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