(R)-1-(1-phenylethyl)urea → (R)-1-(4-Formyl-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea

HRID 588202Notes

Reaction equation

HRID 588202 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH:8]=[O:9])[C:5]2[C:10]([O:32][CH3:33])=[N:11][N:12]([C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:4]=2[CH:3]=1.[C:34]1([C@H:40]([NH:42][C:43]([NH2:45])=[O:44])[CH3:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[CH:8]([C:6]1[C:5]2[C:10]([O:32][CH3:33])=[N:11][N:12]([C:13]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:4]=2[CH:3]=[C:2]([NH:45][C:43]([NH:42][C@@H:40]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH3:41])=[O:44])[N:7]=1)=[O:9]

Participants

3

Reactant 2

HCID 13013340(R)-1-(1-phenylethyl)ureaHCID 1182719996-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbaldehyde2×

Product 1

HCID 118271861(R)-1-(4-Formyl-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea

Procedure

In a manner similar to that described previously (e.g. Scheme 3/Method A and Example 40), 6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbaldehyde (Intermediate 11B) was reacted with converted to (R)-1-(1-phenylethyl)urea (BrettPhos PreCatalyst, cesium carbonate, dioxane, 90° C. for 4 hrs) to provide (R)-1-(4-formyl-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea. MS: [M+H]+ m/z 582.

Sources & evidence

ORD record
ord-b1f2491f14464db5baf4a654abfafdb2
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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