5-tert-Butyl-2-(2-(hydroxymethyl)-3-(1-methyl-6-oxo-5-(pyrimidin-4-ylamino)-1,6-dihydropyridazin-3-yl)phenyl)isoindolin-1-one → tert-Butyl 3-(3-(6-(3-(5-tert-butyl-1-oxoisoindolin-2-yl)-2-(hydroxy-methyl)phenyl)-2-methyl-3-oxo-2,3-dihydropyridazin-4-ylamino)-1H-pyrazol-1-yl)-azetidine-1-carboxylate

HRID 872159Notes

Reaction equation

HRID 872159 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[N:9]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17](C3C=C(NC4C=CN=CN=4)C(=O)N(C)N=3)[C:16]=1[CH2:36][OH:37])[CH2:8]2)([CH3:4])([CH3:3])[CH3:2].Cl[C:39]1[CH:40]=[C:41]([NH:47][C:48]2[CH:52]=[CH:51][N:50]([CH:53]3[CH2:56][N:55]([C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])[CH2:54]3)[N:49]=2)[C:42](=[O:46])[N:43]([CH3:45])[N:44]=1.C(OCC1C(B2OC(C)(C)C(C)(C)O2)=CC=CC=1N1CC2C(=CC=C(C(C)(C)C)C=2)C1=O)(=O)C>>[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[N:9]([C:15]1[C:16]([CH2:36][OH:37])=[C:17]([C:39]3[CH:40]=[C:41]([NH:47][C:48]4[CH:52]=[CH:51][N:50]([CH:53]5[CH2:56][N:55]([C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])[CH2:54]5)[N:49]=4)[C:42](=[O:46])[N:43]([CH3:45])[N:44]=3)[CH:18]=[CH:19][CH:20]=1)[CH2:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 569291425-tert-Butyl-2-(2-(hydroxymethyl)-3-(1-methyl-6-oxo-5-(pyrimidin-4-ylamino)-1,6-dihydropyridazin-3-yl)phenyl)isoindolin-1-oneHCID 66634723tert-Butyl 3-(3-(6-Chloro-2-methyl-3-oxo-2,3-dihydropyridazin-4-ylamino)-1H-pyrazol-1-yl)azetidine-1-carboxylateHCID 866979362-(5-tert-Butyl-1-oxoisoindolin-2-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl Acetate

Product 1

HCID 86697938tert-Butyl 3-(3-(6-(3-(5-tert-butyl-1-oxoisoindolin-2-yl)-2-(hydroxy-methyl)phenyl)-2-methyl-3-oxo-2,3-dihydropyridazin-4-ylamino)-1H-pyrazol-1-yl)-azetidine-1-carboxylate

Procedure

Using the same general procedure as described for the preparation of 103, reaction of 105c (150 mg, 0.394 mmol) with 102f (201 mg, 0.433 mmol) afforded a crude product 105d which was used in the next step without purification.

Sources & evidence

ORD record
ord-0286dcedfdbc4ef781dfd82800592641
Source dataset
uspto-grants-2015_03
Patent number
US08975260B2

Reaction notes

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