HCID 67125929, compound → HCID 54760235, compound

HRID 929993Notes

Reaction equation

Cl.[C:2]([C:6]1[O:10][N:9]=[C:8]([NH:11][C:12](=[O:36])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:35])[C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][C@@H:30]4[CH2:34][CH2:33][NH:32][CH2:31]4)=[CH:24][N:23]=3)=[CH:16][CH:15]=2)[CH:7]=1)([CH3:5])([CH3:4])[CH3:3].Cl.F[CH2:39][C:40](C1ON=C(NC(=O)NC2C=CC(NC(=O)C3C=CC(OC4CCNCC4)=CN=3)=CC=2)C=1)(C)[CH2:41]F>>[C:2]([C:6]1[O:10][N:9]=[C:8]([NH:11][C:12](=[O:36])[NH:13][C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21](=[O:35])[C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][C@@H:30]4[CH2:34][CH2:33][N:32]([CH:40]([CH3:41])[CH3:39])[CH2:31]4)=[CH:24][N:23]=3)=[CH:18][CH:19]=2)[CH:7]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

Reactant 2

HCID 67125929HCID 67125929, compound

HCID 86702370HCID 86702370, compound

Product 1

HCID 54760235HCID 54760235, compoundYield 20%

Procedure

(R)-N-(4-(3-(5-tert-Butylisoxazol-3-yl)ureido)phenyl)-5-((1-isopropylpyrrolidin-3-yl)methoxy)picolinamide (26 mg, 20%) was prepared using a procedure analogous to that described in Example 20, substituting (R)-N-(4-(3-(5-tert-butylisoxazol-3-yl)ureido)phenyl)-5-(pyrrolidin-3-ylmethoxy)picolinamide hydrochloride from Step 2 of this example for N-(4-(3-(5-(1,3-difluoro-2-methylpropan-2-yl)isoxazol-3-yl)ureido)phenyl)-5-(piperidin-4-yloxy)picolinamide hydrochloride used in Example 20. LC-MS (ESI) m/z 521 (M+H)+.

Sources & evidence

ORD record: ord-0cc6b6c0ea8548e587e195f2538103a4
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296722B2

Reaction notes

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