HCID 67125832, compound → HCID 54761680, compound

HRID 929974Notes

Reaction equation

Cl.[C:2]([C:6]1[O:10][N:9]=[C:8]([NH:11][C:12](=[O:35])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:34])[C:22]3[CH:27]=[CH:26][C:25]([O:28][CH:29]4[CH2:33][CH2:32][NH:31][CH2:30]4)=[CH:24][N:23]=3)=[CH:16][CH:15]=2)[CH:7]=1)([CH3:5])([CH3:4])[CH3:3].Cl.F[CH2:38][C:39](C1ON=C(NC(=O)NC2C=CC(NC(=O)C3C=CC(OC4CCNCC4)=CN=3)=CC=2)C=1)(C)[CH2:40]F>>[C:2]([C:6]1[O:10][N:9]=[C:8]([NH:11][C:12](=[O:35])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:34])[C:22]3[CH:27]=[CH:26][C:25]([O:28][CH:29]4[CH2:33][CH2:32][N:31]([CH:39]([CH3:40])[CH3:38])[CH2:30]4)=[CH:24][N:23]=3)=[CH:16][CH:15]=2)[CH:7]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

Reactant 2

HCID 67125832HCID 67125832, compound

HCID 67125929HCID 67125929, compound

Product 1

HCID 54761680HCID 54761680, compoundYield 27%

Procedure

N-(4-(3-(5-tert-Butylisoxazol-3-yl)ureido)phenyl)-5-(1-isopropylpyrrolidin-3-yloxy)picolinamide (30 mg, 27%) was prepared using a procedure analogous to that described Example 20, substituting N-(4-(3-(5-tert-butylisoxazol-3-yl)ureido)phenyl)-5-(pyrrolidin-3-yloxy)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 507 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 10.39 (s, 1H), 9.58 (br. s., 1H), 8.89 (br. s., 1H), 8.33 (br. s., 1H), 8.08 (d, J=8.48 Hz, 1H), 7.81 (d, J=8.48 Hz, 2H), 7.56 (d, J=8.67 Hz, 1H), 7.42 (d, J=8.29 Hz, 2H), 6.50 (s, 1H), 5.05 (br. s., 1H), 2.84-2.95 (m, 1H), 2.69-2.84 (m, 2H), 2.21-2.47 (m, 3H), 1.69-1.87 (m, 1H), 1.30 (s, 9H), 1.03 (d, J=5.65 Hz, 6H).

Sources & evidence

ORD record: ord-da76286d1fdb4e00bfec735ce6911ae5
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296722B2

Reaction notes

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