2-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine → HCID 66711431, compound

HRID 1262126Notes

Reaction equation

HRID 1262126 reaction equation
CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[N:6]2[N:5]=1)=O.[CH3:21][O:22][C:23]1[CH:28]=[C:27]([N:29]2[CH2:35][CH2:34][CH2:33][N:32]([CH:36]3[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]3)[CH2:31][CH2:30]2)[CH:26]=[CH:25][C:24]=1[NH2:43].COC1C=C(C2CCN(C[C@H](OC3N=CC4=CC=C(C5C=CC=CC=5OC)N4N=3)C(F)(F)F)CC2)C=CC=1N>>[CH3:21][O:22][C:23]1[CH:28]=[C:27]([N:29]2[CH2:35][CH2:34][CH2:33][N:32]([CH:36]3[CH2:37][CH2:38][N:39]([CH3:42])[CH2:40][CH2:41]3)[CH2:31][CH2:30]2)[CH:26]=[CH:25][C:24]=1[NH:43][C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[N:6]2[N:5]=1

Participants

4

Reactant 3

HCID 667107912-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazineHCID 66711807HCID 66711807, compoundHCID 66712157HCID 66712157, compound

Product 1

HCID 66711431HCID 66711431, compound

Procedure

Following the experimental procedure described in Example 753, 2-methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine and 2-methoxy-4-[4-(1-methyl-piperidin-4-yl)-perhydro-1,4-diazepin-1-yl]-phenylamine were converted to 2-methoxy-4-(1-{(S)-3,3,3-trifluoro-2-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yloxy]-propyl}-piperidin-4-yl)-phenylamine as a yellow solid (61 mg, 46%). MP: 71-80° C.; 1H-NMR (CDCl3) δ 8.64 (s, 1H), 8.13 (d, J=8.7 Hz, 1H), 8.06 (d, J=7.6 Hz, 1H), 7.40 (m, 1H), 7.15 (s, 1H), 7.11 (m, 1H), 7.05 (d, J=8.4 Hz, 1H), 7.00 (d, J=2.5 Hz, 1H), 6.78 (d, J=3.2 Hz, 1H), 6.27 (s, 1H), 6.18 (d, J=8.8 Hz, 1H), 3.86 (s, 3H), 3.84 (s, 3H), 3.50 (br s, 4H), 2.87 (m, 4H), 2.64 (br s, 2H), 2.47 (m, 1H), 2.25 (s, 3H), 1.93 (m, 4H), 1.72 (m, 2H), 1.61 (m, 2H); LC/MS (ESI+): 542.3 (M+H).

Sources & evidence

ORD record
ord-26f193ed3758434582878074d4782fca
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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