Phthalic Anhydride → HCID 118271799, compound

HRID 590812Notes

Reaction equation

[NH2:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([NH:11][C:12]([NH:14][C@@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])=[O:13])=[CH:10][C:5]=2[N:4]([C:23]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:3]=1.[C:42]1(=O)[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:44](=[O:51])[O:43]1>O1CCOCC1>[O:43]=[C:42]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:44](=[O:51])[N:1]1[C:2]1[C:6]2[CH:7]=[N:8][C:9]([NH:11][C:12]([NH:14][C@@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])=[O:13])=[CH:10][C:5]=2[N:4]([C:23]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

(R)-1-(3-Amino-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (Example 47, Step 1; 503 mg, 0.934 mmol) and isobenzofuran-1,3-dione (159 mg, 1.074 mmol) were added to a 1.5 mL microwave vial, charged with dioxane (4 mL), and heated to 110° C. for 4.5 h. The solvents were concentrated in vacuo and the residue was purified by flash chromatography (2-10% EtOAc/DCM) to give (R)-1-(3-(1,3-dioxoisoindolin-2-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea. MS ESI calc'd. for C42H32N6O3 [M+1]+ 669. found 669.

Workup

concentrationThe solvents were concentrated in vacuo
customthe residue was purified by flash chromatography (2-10% EtOAc/DCM)

Sources & evidence

ORD record: ord-a80b5ca1375a4d5aabc35e2bf8ecfcc1
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233979B2

Reaction notes

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