HCID 117720537, compound → (+/-)-[4-(3,3-Difluoro-piperidin-4-yl)-2-methoxy-phenyl]-[7-(2-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine

HRID 60374Notes

Reaction equation

HRID 60374 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]2[N:17]3[C:12]([CH:13]=[N:14][C:15](O)=[N:16]3)=[CH:11][CH:10]=2)=[CH:7][CH:6]=[CH:5][N:4]=1.C(OC([N:26]1[CH2:31][CH2:30][CH:29]([C:32]2[CH:37]=[CH:36][C:35]([NH2:38])=[C:34]([O:39][CH3:40])[CH:33]=2)[C:28]([F:42])([F:41])[CH2:27]1)=O)(C)(C)C>>[F:42][C:28]1([F:41])[CH:29]([C:32]2[CH:37]=[CH:36][C:35]([NH:38][C:15]3[N:14]=[CH:13][C:12]4=[CH:11][CH:10]=[C:9]([C:8]5[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=5)[N:17]4[N:16]=3)=[C:34]([O:39][CH3:40])[CH:33]=2)[CH2:30][CH2:31][NH:26][CH2:27]1

Participants

3

Reactant 2

HCID 117720537HCID 117720537, compoundHCID 1784940927-(2-Methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol

Product 1

HCID 86581723(+/-)-[4-(3,3-Difluoro-piperidin-4-yl)-2-methoxy-phenyl]-[7-(2-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine

Procedure

7-(2-Methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol (prepared as described in U.S. Pat. No. 8,471,005/Appl. WO2010071885; 65 mg, 0.27 mmol) and (±)-4-(4-amino-3-methoxy-phenyl)-3,3-difluoro-piperidine-1-carboxylic acid tert-butyl ester (100 mg, 0.29 mmol) were converted to the title compound by a procedure similar to Example 4, to afford a yellow foam (86 mg, 69% yield). 1H NMR (CDCl3): 8.72 (s, 1H), 8.49 (d, J=7.4 Hz, 1H), 8.28 (d, J=8.2 Hz, 1H), 8.24 (m, 1H), 7.51 (s, 1H), 7.14 (d, J=4.0 Hz, 1H), 7.08 (m, 1H), 6.86 (m, 3H), 4.02 (s, 3H), 3.92 (s, 3H), 3.30 (m, 1H), 3.21 (m, 1H), 3.02 (m, 1H), 2.90 (dd, J=30.8 (F_H vic. coupling), 13.7 Hz, 1H), 2.75 (m, 1H), 2.10 (m, 1H), 1.95 (m, 2H); LC/MS (ESI+): 467.0 (M+H).

Sources & evidence

ORD record
ord-27fa36bc943d4e17a434e5c7824459bf
Source dataset
uspto-grants-2016_09
Patent number
US09440984B2

Reaction notes

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