1-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol → 3-cyclopentyl-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-2-(1-oxo-1H-phthalazin-2-yl)-propionamide

HRID 2381503Notes

Reaction equation

HRID 2381503 reaction equation
[CH:1]1([CH2:6][CH:7]([N:11]2[N:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:22][C:23]1[CH:27]=[CH:26][N:25]([CH2:28][C:29]([CH3:32])([OH:31])[CH3:30])[N:24]=1>>[CH:1]1([CH2:6][CH:7]([N:11]2[N:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[C:8]([NH:22][C:23]2[CH:27]=[CH:26][N:25]([CH2:28][C:29]([OH:31])([CH3:30])[CH3:32])[N:24]=2)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 593449381-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol2×HCID 66891968HCID 66891968, compound

Product 1

HCID 579192303-cyclopentyl-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-2-(1-oxo-1H-phthalazin-2-yl)-propionamideYield 11%

Procedure

Using the method described in Example 83, Step 3,3-cyclopentyl-2-(1-oxo-1H-phthalazin-2-yl)-propionic acid (as prepared in Example 83, Step 2) and 1-(3-amino-pyrazol-1-yl)-2-methyl-propan-2-ol (Intermediate 1) afforded 3-cyclopentyl-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-2-(1-oxo-1H-phthalazin-2-yl)-propionamide as a white solid (48 mg, 11%); ES+-HRMS m/e calcd for C23H29N5O3 [M+H+] 319.1223 found 319.1223. 1H-NMR (300 MHz, DMSO-d6) δ ppm 1.03 (s, 6H), 1.04-1.17 (m, 1H), 1.24-1.72 (m, 8H), 1.93-2.10 (m, 1H), 2.21-2.35 (m, 1H), 3.86 (s, 2H), 4.64 (s, 1H), 5.61 (dd, J=10.7, 4.1 Hz, 1H), 6.39 (d, J=2.1 Hz, 1H), 7.50 (d, J=2.1 Hz, 1H), 7.79-7.91 (m, 1H), 7.91-7.98 (m, 2H), 8.24 (d, J=7.5 Hz, 1H), 8.48 (s, 1H), 10.66 (s, 1H).

Sources & evidence

ORD record
ord-11bc014af6144b2298ce15bccff7c161
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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