HCID 54589424, compound → HCID 54761503, compound

HRID 929969Notes

Reaction equation

Cl.[F:2][CH2:3][C:4]([C:8]1[O:12][N:11]=[C:10]([NH:13][C:14](=[O:38])[NH:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:37])[C:24]3[CH:29]=[CH:28][C:27]([O:30][CH:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)=[CH:26][N:25]=3)=[CH:18][CH:17]=2)[CH:9]=1)([CH3:7])[CH2:5][F:6].Cl.[C:40](C1ON=C(NC(=O)NC2C=CC(NC(=O)C3C=C(OC4CCNCC4)C=CN=3)=CC=2)C=1)(C)(C)[CH3:41]>>[F:2][CH2:3][C:4]([C:8]1[O:12][N:11]=[C:10]([NH:13][C:14](=[O:38])[NH:15][C:16]2[CH:17]=[CH:18][C:19]([NH:22][C:23](=[O:37])[C:24]3[CH:29]=[CH:28][C:27]([O:30][CH:31]4[CH2:32][CH2:33][N:34]([CH2:40][CH3:41])[CH2:35][CH2:36]4)=[CH:26][N:25]=3)=[CH:20][CH:21]=2)[CH:9]=1)([CH3:7])[CH2:5][F:6]

Participants

Reactant 2

HCID 54589424HCID 54589424, compound

HCID 67125929HCID 67125929, compound

Product 1

HCID 54761503HCID 54761503, compoundYield 94%

Procedure

N-(4-(3-(5-(1,3-Difluoro-2-methylpropan-2-yl)isoxazol-3-yl)ureido)phenyl)-5-(1-ethylpiperidin-4-yloxy)picolinamide (65 mg, 94%) was prepared as a white powder using a procedure analogous to that described in Example 2, substituting N-(4-(3-(5-(1,3-difluoro-2-methylpropan-2-yl)isoxazol-3-yl)ureido)phenyl)-5-(piperidin-4-yloxy)picolinamide hydrochloride from Step 3 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 543 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 10.40 (s, 1H), 9.60 (s, 1H), 8.79 (s, 1H), 8.38 (s, 1H), 8.10 (d, J=8.85 Hz, 1H), 7.81 (d, J=9.04 Hz, 2H), 7.63-7.72 (m, 1H), 7.42 (d, J=9.04 Hz, 2H), 6.79 (s, 1H), 4.73 (s, 2H), 4.58 (s, 2H), 2.73 (br. s., 1H), 2.27 (br. s., 3H), 1.97-2.17 (m, 2H), 1.91 (s, 2H), 1.75 (s, 2H), 1.34 (s, 3H), 0.90-1.20 (m, 4H).

Sources & evidence

ORD record: ord-67b6b8a6a064466bb13d0c18a9681f19
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296722B2

Reaction notes

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