HCID 54589424, compound → HCID 54759301, compound

HRID 929983Notes

Reaction equation

Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][C:28]4[CH:32]=[C:31]([C:33]([CH3:39])([CH3:38])[C:34]([F:37])([F:36])[F:35])[O:30][N:29]=4)=[O:26])=[CH:20][CH:19]=3)=[O:16])=[N:13][CH:14]=2)[CH2:4][CH2:3]1.Cl.[C:41](C1ON=C(NC(=O)NC2C=CC(NC(=O)C3C=C(OC4CCNCC4)C=CN=3)=CC=2)C=1)(C)(C)[CH3:42]>>[CH2:41]([N:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]([NH:17][C:18]3[CH:19]=[CH:20][C:21]([NH:24][C:25]([NH:27][C:28]4[CH:32]=[C:31]([C:33]([CH3:39])([CH3:38])[C:34]([F:37])([F:35])[F:36])[O:30][N:29]=4)=[O:26])=[CH:22][CH:23]=3)=[O:16])=[N:13][CH:14]=2)[CH2:4][CH2:3]1)[CH3:42]

Participants

Reactant 2

HCID 54589424HCID 54589424, compound

HCID 67125935HCID 67125935, compound

Product 1

HCID 54759301HCID 54759301, compoundYield 68%

Procedure

5-(1-Ethylpiperidin-4-yloxy)-N-(4-(3-(5-(1,1,1-trifluoro-2-methylpropan-2-yl)isoxazol-3-yl)ureido)phenyl)picolinamide (79 mg, 68%) was prepared using a procedure analogous to that described in Example 2, substituting 5-(piperidin-4-yloxy)-N-(4-(3-(5-(1,1,1-trifluoro-2-methylpropan-2-yl)isoxazol-3-yl)ureido)phenyl)picolinamide hydrochloride from Step 2 of this example for N-(4-(3-(5-tert-butylisoxazol-3-yl)ureido)phenyl)-4-(piperidin-4-yloxy)picolinamide hydrochloride used in Example 2. LC-MS (ESI) m/z 561 (M+H)+.

Sources & evidence

ORD record: ord-5737ae6268e04d5fa7fe1e9c5375ad5b
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296722B2

Reaction notes

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