7-amino-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-methyl-2,3-dihydro-1H-isoindol-1-one → 7-amino-4-(1-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-1H-pyrazol-4-yl)-2-methyl-2,3-dihydro-1H-isoindol-1-one

HRID 2279721Notes

Reaction equation

HRID 2279721 reaction equation
NC1C=CC(C2C=NN(CCCO)C=2)=C2C=1C(=O)N(C)C2.[CH3:22][C:23]1([CH3:48])[O:27][C@@H:26]([CH2:28][N:29]2[CH:33]=[C:32]([C:34]3[CH:42]=[CH:41][C:40]([N+:43]([O-])=O)=[C:39]4[C:35]=3[CH2:36][N:37]([CH3:47])[C:38]4=[O:46])[CH:31]=[N:30]2)[CH2:25][O:24]1>>[NH2:43][C:40]1[CH:41]=[CH:42][C:34]([C:32]2[CH:31]=[N:30][N:29]([CH2:28][C@H:26]3[CH2:25][O:24][C:23]([CH3:48])([CH3:22])[O:27]3)[CH:33]=2)=[C:35]2[C:39]=1[C:38](=[O:46])[N:37]([CH3:47])[CH2:36]2

Participants

3

Reactant 2

HCID 672551227-amino-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-methyl-2,3-dihydro-1H-isoindol-1-oneHCID 678119154-(1-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-1H-pyrazol-4-yl)-2-methyl-7-nitro-2,3-dihydro-1H-isoindol-1-one2×

Product 1

HCID 678116527-amino-4-(1-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-1H-pyrazol-4-yl)-2-methyl-2,3-dihydro-1H-isoindol-1-oneYield 90%

Procedure

Prepared analogously to Compound 1C replacing Compound 1D with 4-(1-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-1H-pyrazol-4-yl)-2-methyl-7-nitro-2,3-dihydro-1H-isoindol-1-one (Compound 5D, 1.96 g) to afford 1.03 g of the desired product (90%). 1H NMR (400 MHz, DMSO-d6) δ 7.96 (d, J=0.5 Hz, 1H), 7.75 (d, J=0.8 Hz, 1H), 7.43 (d, J=8.3 Hz, 1H), 6.62 (d, J=8.3 Hz, 1H), 6.07 (s, 2H), 4.38-4.47 (m, 3H), 4.24 (dd, J=1.4, 5.7 Hz, 2H), 4.01 (dd, J=6.3, 8.6 Hz, 1H), 3.78 (dd, J=5.7, 8.5 Hz, 1H), 3.03 (s, 3H), 1.24-1.35 (m, 6H). MS (ESI): m/z 343.15 [M+H]+. UPLC: tR=1.09 min (UPLC-TOF: polar—3 min).

Sources & evidence

ORD record
ord-4090cccccfc143cb989174771f1b8c1e
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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