HCID 67125872, compound → HCID 54761678, compound

HRID 929973Notes

Reaction equation

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

Participants

Reactant 2

HCID 67125872HCID 67125872, compound

HCID 67125929HCID 67125929, compound

Product 1

HCID 54761678HCID 54761678, compoundYield 19%

Procedure

N-(4-(3-(5-tert-Butylisoxazol-3-yl)ureido)phenyl)-5-(1-isopropylazetidin-3-yloxy)picolinamide (25 mg, 19%) was prepared as an off-white powder using a procedure analogous to that described in Example 20, substituting 5-(azetidin-3-yloxy)-N-(4-(3-(5-tert-butylisoxazol-3-yl)ureido)phenyl)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 493 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 10.40 (s, 1H), 9.48 (s, 1H), 8.78 (s, 1H), 8.31 (s, 1H), 8.08 (dd, J=1.32, 8.67 Hz, 1H), 7.81 (d, J=7.35 Hz, 2H), 7.50 (dd, J=2.64, 8.67 Hz, 1H), 7.41 (d, J=7.16 Hz, 2H), 6.50 (d, J=1.88 Hz, 1H), 4.94 (t, J=5.46 Hz, 1H), 3.73 (t, J=6.40 Hz, 2H), 3.00 (t, J=6.03 Hz, 2H), 2.29-2.41 (m, 1H), 1.29 (d, J=1.88 Hz, 9H), 0.77-0.95 (m, 6H).

Sources & evidence

ORD record: ord-3e52894fb664451f82d8840389637da5
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296722B2

Reaction notes

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